South Woods, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in South Woods, Massachusetts on RentalSaver.com!

South Woods Rentals

From $663 per night (USD)
VRBO
Luxury Home in the Heart of Rockport
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Gorgeous house in Rockport, steps to beach, town, train, Shalin Liu performance center! This home is located on a quiet ...
From $663 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly remodeled, this spacious & immaculate king-size suite has lovely views of the ocean from your perch above the tree ...
From $249 per night (USD)
Expedia
From $1149 per night (USD)
VRBO
Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
This is the Vacation Beach House you have been searching for. Perfectly located only steps to Long Beach Gloucester, thi ...
From $1149 per night (USD)
VRBO
From $223 per night (USD)
VRBO
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Immerse yourself in the heart of America's most famous seaside artists' colony. Located on Bearskin Neck and nestled in ...
From $223 per night (USD)
VRBO
From $412 per night (USD)
VRBO
Sea Glass House - Tranquil Retreat or Base for Adventure
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Whether you seek a tranquil seaside retreat or a base for adventure, this immaculate first floor apartment has 2 large s ...
From $412 per night (USD)
VRBO
From $400 per night (USD)
VRBO
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
My husband and I want to assure you that we take your family's health and safety very seriously. Our house is professio ...
From $400 per night (USD)
VRBO
From $372 per night (USD)
VRBO
Quaint Simplicity on Quiet Lane, Spacious and Relaxing, Walk to Shops, Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This peaceful location on a quiet lane just outside of Rockport's downtown offers an easy place from which to enjoy the ...
From $372 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Perfect Rockport Downtown Vacation Destination
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our fully renovated 3 bedroom cottage style unit offers all of the amenities needed for a perfect Rockport vacation. Ent ...
From $419 per night (USD)
Expedia
From $542 per night (USD)
VRBO
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This recently renovated beach themed 3 level, 3 bedroom, 2.5 baths, fully stocked condo, has 2 unique outdoor spaces, an ...
From $542 per night (USD)
VRBO
From $354 per night (USD)
VRBO
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to a historical harborside treasure at our breathtaking 3rd-floor walk-up. As you step into the unit, prepare to ...
From $354 per night (USD)
VRBO
From $787 per night (USD)
VRBO
The Spinnaker: A hidden gem in Rockport village with roof deck and a garden.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Rockport village, The Spinnaker is the perfect rental home to feel worlds away from it all with a delightful ...
From $787 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Walk To Good Harbor, OCEAN VIEWS, Open All Year!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: You and your family cannot beat this amazing Gloucester location, walking distance to the best beach in all of ...
From $476 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Ocean Views in this Charming 2 bedroom Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Charming two bedroom cottage. The property has a wonderful open kitchen and dining room that gives way to an ocean facin ...
From $369 per night (USD)
VRBO
From $184 per night (USD)
Expedia
cozy townhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
very cute space,2 floors, central to beaches, downtown,shops,restaurants,1 bedroom,1 bath, small porch on the front, sma ...
From $184 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Experience seaside charm near Good Harbor Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Come and enjoy this new home with roof top deck overlooking Good Harbor Beach. We are a 5 minute walk to the beach! We ...
From $550 per night (USD)
VRBO
From $244 per night (USD)
VRBO
Gladview Rockport Apt #gladview#thacher
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Thacher Island and the twin light houses. Welcome to Rockport by the sea with Loblolly Cove 4 houses away. Open concep ...
From $244 per night (USD)
VRBO
From $239 per night (USD)
VRBO
Holbrook House: Charming Rockport Village House, Walk To Everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A cozy, lovingly restored 1950's house. Walking distance to all that Rockport village and Bear Skin Neck has to offer. ...
From $239 per night (USD)
VRBO
From $652 per night (USD)
VRBO
Brilliant Ocean Views. Two Cottages - One price.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
'Back Beach Cottages' is a unique property with a two cottage set up. Both houses have wonderful views of the ocean and ...
From $652 per night (USD)
VRBO
From $237 per night (USD)
VRBO
Sea Mist Cottage, Rockport, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
SeaMist Cottage is located on a private yard in historic downtown Rockport, Massachusetts, a charming seaside community. ...
From $237 per night (USD)
VRBO
From $370 per night (USD)
VRBO
Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our adorable, 3 bedroom home is in a prime location for your vacation, with plenty of windows for ocean breezes. If yo ...
From $370 per night (USD)
VRBO
From $407 per night (USD)
VRBO
Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to our charming 3-bedroom vacation home in the heart of Rockport! Nestled just a short walk from the Shalin Liu ...
From $407 per night (USD)
VRBO
From $497 per night (USD)
Expedia
Beach cottage walkable to Good Harbor and Long Beach- RENOVATED!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summer at its best! A delightful spot near the beach, nice private fenced in backyard, walkable to Long Beach and Good H ...
From $497 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Charming year round cottage - Pet Friendly with Wi-Fi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Please contact us for more details. We would love to discuss your vacation plans at our Home Away from Home. We are Pe ...
From $495 per night (USD)
VRBO
From $250 per night (USD)
Expedia
Peaceful Cottage Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
A one bedroom, one bath, contemporary home features a light filled open floor plan. Located on a perfect road for walk ...
From $250 per night (USD)
Expedia
From $727 per night (USD)
VRBO
Private, Single Family Beach House, Right at Good Harbor Beach foot bridge
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
*Please; CONTACT HOST FOR MULTI-MONTH and OFF SEASON RATES* Real beach house on one of Boston areas most beautiful an ...
From $727 per night (USD)
VRBO
From $130 per night (USD)
VRBO
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Om Suite Om is a comfortable, cozy and convenient studio efficiency space, with a separate key and entry, in the lower l ...
From $130 per night (USD)
VRBO
From $496 per night (USD)
VRBO
Beautiful Newly Built Custom Home, Spectacular Ocean Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This luxurious, 3-year-old, ocean-view, custom home is found in the New England seaside town of Rockport. Windows surro ...
From $496 per night (USD)
VRBO
From $656 per night (USD)
Expedia
Beautiful vacation home. Reduced mos rates Oct-May. Plz contact for details.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to our charming 3-bedroom vacation home in the heart of Rockport, just a short walk from the Shalin Liu Performan ...
From $656 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Long Beach Gloucester 2 minute walk to Beach.Large yard & lush gardens. Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The weeks of July 19 - 26 and August 16 - 23 have just opened up! This is your chance to enjoy Long Beach, only a few ...
From $527 per night (USD)
VRBO
From $184 per night (USD)
VRBO
Seaside vacation studio steps from beaches and harbor area in historic Rockport
Bedrooms:
3
Bathrooms:
1
Sleeps:
2
RESERVATIONS NOW BEING ACCEPTED FOR SUMMER 2023 starting May through October! Ground floor efficiency studio private r ...
From $184 per night (USD)
VRBO
From $391 per night (USD)
VRBO
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy your vacation sojourn in this newly-renovated home, a short walk to one of New England's most beautiful beaches. ...
From $391 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Seaside Escape just steps to Good Harbor beach in Gloucester
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Charming 2 bedroom home located on a quiet Cul de Sac that's just steps to beautiful Good Harbor Beach. Completely renov ...
From $461 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Charming Pet Friendly Studio Cottage On Quiet Lane
Bedrooms:
1
Bathrooms:
0
Sleeps:
0
Step away from your hectic life. Welcome to our homes by the sea. The scent of the ocean. The crack of a lobster claw. S ...
From $234 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Quaint Waterfront Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Relax and breathe the salt air in this charming waterfront cottage. It is on well-known Bearskin Neck with a large deck ...
From $208 per night (USD)
VRBO
$Waterfront House on Rockport’s \nOld Harbour Enjoy Spectacular Views$
From $443 per night (USD)
VRBO
Waterfront House on Rockport’s \nOld Harbour Enjoy Spectacular Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This historical, 19th-century comfortable waterfront house is located in the heart of Rockport directly on Rockport's O ...
From $443 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Picturesque Rockport Queen Anne Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Great location in beautiful Rockport. The house is a ten minute walk into town - Bearskin Neck shopping, art galleries, ...
From $275 per night (USD)
VRBO
From $184 per night (USD)
VRBO
✩1 min to Front Beach✩Cute Studio✩Prime location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
➤NEW wood tile throughout, exposed brick feels like a tiny home. ➤Brand new Queen size Murphy bed ➤sitting area, flat s ...
From $184 per night (USD)
VRBO
From $352 per night (USD)
Expedia
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Look no further! Enjoy being a guest at this stylish beach bungalow! It is the perfect vacation spot for you and your fa ...
From $352 per night (USD)
Expedia
From $286 per night (USD)
VRBO
Dog-friendly apartment in a prime location - walk to town beaches
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Olde New House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $286 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Twin Lights: Explore the village of Rockport!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy coastal living in the beautiful historical town of Rockport. Twin Lights is a charming and recently renovated cott ...
From $436 per night (USD)
Expedia
From $624 per night (USD)
VRBO
Sea Glass on South: Modern rustic chic, just steps from downtown Rockport
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Nestled on the edge of the village of Rockport, Sea Glass on South is a brand new and modern retreat, inspired by the Ne ...
From $624 per night (USD)
VRBO
From $1688 per night (USD)
Expedia
Spectacular, luxury waterfront property directly overlooking Sandy Bay.
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
This impressive and generously proportioned contemporary residence, situated within walking distance of several local be ...
From $1688 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Newly renovated! Beautiful private cottage in quiet area near Old Garden Beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Completely renovated house in Rockport’s desirable South End. Our home is located in a wonderful neighborhood for walki ...
From $357 per night (USD)
VRBO
From $493 per night (USD)
Expedia
'We can't wait to return to Four Winds'
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PARKING SPOT 10 SECOND WALK AWAY, Four Winds is a two bedroom condo located directly on Tuna Wharf. If you love the sou ...
From $493 per night (USD)
Expedia
From $812 per night (USD)
VRBO
Lovely Oceanfront 4-Bedroom on Private Road
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Gorgeous ocean views from almost every window and peaceful privacy at this delightful house about a mile from the center ...
From $812 per night (USD)
VRBO
From $717 per night (USD)
VRBO
Spacious Modern Beach House- Steps to Long Beach and Good Harbor
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Just steps to Long Beach, or a 10 minute walk to Good Harbor Beach, enjoy this clean, modern new single family home with ...
From $717 per night (USD)
VRBO
From $437 per night (USD)
VRBO
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Just 4/10 of a mile from Gloucester's sandy Good Harbor Beach, Joseph's Way is delightful two bedroom property is nestle ...
From $437 per night (USD)
VRBO
From $617 per night (USD)
VRBO
Good Harbor Beachfront at the Footbridge
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Single family house, over one hundred years old, accommodates ten. Three queen beds, one double bed with a trundle, and ...
From $617 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vintage Rockport Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $320 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Oceanfront home right on Long Beach near town & whale watching with tennis
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Oceanfront Cottage - Long Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $367 per night (USD)
Expedia
From $882 per night (USD)
VRBO
The Aerie. 2 King beds, AC, outdoor shower. Walk to 2 local beaches
Bedrooms:
2
Bathrooms:
8
Sleeps:
16
Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your lif ...
From $882 per night (USD)
VRBO
From $658 per night (USD)
VRBO
Sweet, Bright, Water Views & 2 min walk to Beach Discounts available see below
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come and make memories of a lifetime!! Easy living open floor plan, beachy bright and steps to Cape Hedge Beach and Long ...
From $658 per night (USD)
VRBO
From $745 per night (USD)
VRBO
Fantastic ocean views and 2 great beaches
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Ocean Crag has gorgeous ocean views and is located steps away from Cape Hedge and Long Beaches. Enjoy breathtaking view ...
From $745 per night (USD)
VRBO
From $1067 per night (USD)
Expedia
Beach & King - Stunning Ocean Views!
Bedrooms:
5
Bathrooms:
8
Sleeps:
14
Located across from Rockport's Front Beach, Beach & King is a beautiful Cape Ann Beach House rental on the North Shore i ...
From $1067 per night (USD)
Expedia
From $303 per night (USD)
VRBO
HEART OF HISTORICAL ROCKPORT with Reserved Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to the perfect romantic harborside retreat in Rockport, you will be mesmerized by the view. This 1,000 sq ft s ...
From $303 per night (USD)
VRBO
From $1226 per night (USD)
Expedia
Seacroft: Classic Victorian home with views of the ocean and twin light houses.
Bedrooms:
3
Bathrooms:
7
Sleeps:
16
This updated and well-cared for Victorian home with its captivating ocean views, sits high on two private acres at the e ...
From $1226 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Walk to Good Harbor Beach, pet friendly, family beach home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy a memorable family vacation in this fully furnished, 3 bedroom single-family home with deck, yard and marsh views, ...
From $318 per night (USD)
VRBO
From $379 per night (USD)
VRBO
STUNNING OCEAN VIEWS FROM OUR 2 BEDROOM COTTAGE
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
"The Seaward" is located in a spectacular setting, (known by some as "the golden road of Rockport"). Spruce Cottage is ...
From $379 per night (USD)
VRBO
From $499 per night (USD)
VRBO
Private Pet Friendly hideaway near the beach and town center.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cottage on the Pond is tucked away from the summer crowds at the end of a picturesque lane with ocean views from the fro ...
From $499 per night (USD)
VRBO
From $466 per night (USD)
VRBO
Super cute Beachfront cottage, steps from beautiful sandy Long Beach
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
This 4 bedroom plus loft, 2 full bathroom cottage is only a few feet from the beautiful and sandy Long Beach in Rockport ...
From $466 per night (USD)
VRBO
$Downtown Home near the Beach & Downtown w\/Gas Grill, Washer\/Dryer & Deck$
From $594 per night (USD)
VRBO
Downtown Home near the Beach & Downtown w\/Gas Grill, Washer\/Dryer & Deck
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
High Street Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $594 per night (USD)
VRBO
From $609 per night (USD)
VRBO
The Haabah Beach Retreat—4 Minute Walk to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Two-bedroom gorgeous beach house overlooking Good Harbor Beach, located DIRECTLY on the Good Harbor estuary. The house i ...
From $609 per night (USD)
VRBO
From $212 per night (USD)
VRBO
Perfect apartment for a single or couple. Short walk to Front Beach and Town.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Private entrance down a crushed stone path ending with a garden patio. Close to beaches, downtown and the commuter train ...
From $212 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Sandy Bay: An oceanfront gem vacation rental with ocean views in Rockport.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to an oceanfront gem with exquisite views of Rockport's Sandy Bay and the Atlantic Ocean. Located just a short di ...
From $386 per night (USD)
Expedia
From $391 per night (USD)
VRBO
The Waterline – A Private Harborfront Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in the historic Sail Loft building on Bearskin Neck, The Waterline offers a charming ground-floor retreat with s ...
From $391 per night (USD)
VRBO
From $603 per night (USD)
VRBO
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come enjoy the ocean in Rockport. Fully furnished 3 bedroom 2 bath charming antique home with updated kitchen and baths. ...
From $603 per night (USD)
VRBO
From $289 per night (USD)
VRBO
You will love our location and will return for our hospitality!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
After the success of A Breezy Cottage, we set our sails on The Life of Reilly! The property was purchased in September, ...
From $289 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Jewel Box: A gem of a rental home close to Good Harbor Beach.
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Situated at the end of a quiet street and down the road from Good Harbor Beach, Jewel Box is a gem of a rental home. Thi ...
From $402 per night (USD)
Expedia
From $798 per night (USD)
VRBO
Sage Hill: Perfectly situated for Long Beach, Gloucester, and Rockport.
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage ...
From $798 per night (USD)
VRBO
$\Absolutely lovely. The cottage, the beach, the town, the owners.\$
From $353 per night (USD)
VRBO
\"Absolutely lovely. The cottage, the beach, the town, the owners.\"
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
A Breezy Cottage is a very short walk to the charming beaches of Rockport, MA. It comfortably sleeps up to 7 people inc ...
From $353 per night (USD)
VRBO
From $661 per night (USD)
VRBO
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Welcome to your very own summer beach home! Located a short 3 minute walk from good harbor beach, this two level single ...
From $661 per night (USD)
VRBO
From $894 per night (USD)
VRBO
Family home – 40 Atlantic Ave., Rockport, MA. Minutes walk to town and beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Leave your car in the driveway and walk to beach and town: 4-minutes to secluded Old Garden Beach, the Atlantic Pat ...
From $894 per night (USD)
VRBO
From $856 per night (USD)
VRBO
Two Beaches: Walk to Long Beach or Good Harbor!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home is a mere 3-minute wa ...
From $856 per night (USD)
VRBO
From $359 per night (USD)
Expedia
Bearskin Neck Rental with 2 private decks!, Bearskin Neck Rental with 2 bed, 1 bath, and 2 private d
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A centrally located two-bedroom apartment above The Pewter Shop on Bearskin Neck offering views of the harbor and downto ...
From $359 per night (USD)
Expedia
$Relax by the Sea – 3BR Rockport Retreat w\/ A\/C & Pets Welcome$
From $346 per night (USD)
VRBO
Relax by the Sea – 3BR Rockport Retreat w\/ A\/C & Pets Welcome
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Just an hour from Boston, this classic New England cottage puts you right in the heart of Rockport—and yes, it’s real (e ...
From $346 per night (USD)
VRBO
From $996 per night (USD)
VRBO
Beach Front Luxe: Italian vibes & coastal glam in Rockport! Steps to Downtown!!!
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
Enjoy a little bit of Italy in Coastal New England! Expansive Atlantic views, and steps to Front Beach, design enthusias ...
From $996 per night (USD)
VRBO
From $646 per night (USD)
VRBO
Spectacular views of Thatcher Island and the Atlantic Ocean
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This home features spectacular views of Thatcher Island’s twin lighthouses, Loblolly Cove and the Atlantic Ocean from th ...
From $646 per night (USD)
VRBO
From $142 per night (USD)
Expedia
Cozy Cottage Old Fashioned Charm
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Walk to beaches from this adorable old fashioned New England Style beach cottage when you book a stay with us. We are ...
From $142 per night (USD)
Expedia
$~Walk to Good Harbor Beach: Adorable 4 bedroom\/2 bath Dog Friendly~AC-Summer fun$
From $489 per night (USD)
VRBO
~Walk to Good Harbor Beach: Adorable 4 bedroom\/2 bath Dog Friendly~AC-Summer fun
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Very sunny, clean and recently updated - 4 bedrooms, 2 bath home, (one bed is in separate in-law with bathroom) ranch, w ...
From $489 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Bell Buoy: Bearskin Neck, Roof Deck, Charming Downtown, Walk to Beach & Eateries, Ocean View
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Bell Buoy, a charming cottage located in the heart of Bearskin Neck. From the rooftop deck, you'll enjoy vie ...
From $318 per night (USD)
VRBO
From $546 per night (USD)
VRBO
Beach Bungalow: The perfect getaway to two of Rockport's finest beaches.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This sweet vacation rental cottage is a short distance to two of Rockport's finest beaches - Cape Hedge and Long Beach. ...
From $546 per night (USD)
VRBO
From $1144 per night (USD)
Expedia
Seaside House: Good Harbor Beach and the Back Shore right outside your door.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Location, location, location! This vacation home is large and comfortable and is just steps to the white sands and surf ...
From $1144 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Rockport, steps to Front Beach, restaurants, shopping
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful fully furnished condo, just steps to Front Beach with ocean views. Accommodations for up to 4 guests, with se ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Woodfall: A serene and tranquil Rockport getaway.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Woodfall is a lovely apartment located in a quiet and leafy residential neighborhood just a short walk to Rockport villa ...
Click For Pricing
Expedia
From $389 per night (USD)
VRBO
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this br ...
From $389 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Majestic summer rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Single family home with ocean view close to Old Garden Beach and Bearskin Neck. Sleeps eight on large spacious property. ...
From $328 per night (USD)
VRBO
From $562 per night (USD)
VRBO
GOT BEACH! Good Harbor House
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Location, Location, Location! Get ready to do some serious relaxing at this beautiful and comfortable, 4 bedroom house ...
From $562 per night (USD)
VRBO
From $656 per night (USD)
VRBO
Ocean Beach Cottage ~ Just Steps Away from Sun Sand & Surf ~
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nothing can compare to a summer vacation in Rockport; especially if its spent on Long Beach! You're sure to feel any st ...
From $656 per night (USD)
VRBO
From $595 per night (USD)
VRBO
Tuna Wharf Townhouse has been sold and is no longer available to rent.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel free to contact me and I can refer you to other STR's Thanks! Jonathan Steps from the junction of Bearskin Ne ...
From $595 per night (USD)
VRBO
From $624 per night (USD)
Expedia
Beautiful 3 bed home...steps from Good Harbor and Long Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Renovate beach home, steps from two of New England's most beautiful beaches, Good Harbor and Long Beach! This beautiful ...
From $624 per night (USD)
Expedia
From $351 per night (USD)
VRBO
Dot's Place: A sunny escape in the heart of Rockport.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This cute and sunny renovated 1BR apartment is located on a quiet lane in the heart of Rockport. Park your car and walk ...
From $351 per night (USD)
VRBO
From $744 per night (USD)
VRBO
Rockport, MA 3 BR 2017 Old Garden Beach Home With Gorgeous Views And Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Built in 2017, great location, steps to Old Garden Beach, Headlands (green space at head of harbor), and downtown. Desi ...
From $744 per night (USD)
VRBO
From $1013 per night (USD)
VRBO
Straitsmouth Cove: Outstanding ocean views at Gap Head Cove in Rockport.
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Straitsmouth Cove is a classic seaside "cottage" in a sublime location on Rockport’s Gap Cove. This elegant vacation hom ...
From $1013 per night (USD)
VRBO
From $757 per night (USD)
Expedia
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean- ...
From $757 per night (USD)
Expedia
From $213 per night (USD)
VRBO
Quaint Home, Near Good Harbor Beach and Town, Great for Families
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
NOTE: We are currently only booking stays through May 2025. Check back later in the year for daily and weekly summer sta ...
From $213 per night (USD)
VRBO
From $812 per night (USD)
Expedia
Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Just up the street from Good Harbor Beach, this well-appointed and perfectly located vacation rental is the ideal home b ...
From $812 per night (USD)
Expedia
From $1627 per night (USD)
VRBO
Golden Sands at Good Harbor: Just walk across the street to the beach.
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Golden Sands is the quintessential turn of the century Gloucester beach "cottage." With views of Good Harbor Beach, the ...
From $1627 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Long Beach Suites: 3 Mins Toes To Sand!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in o ...
From $455 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Long Beach Suites: Ocean Views, Book 2025 Already!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in o ...
From $262 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Long Beach Suites: Book 2025 Summer Trip Today!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Recently built, Long Beach Suites is ready to welcome you this summer. With peaks of Long Beach, come stay in o ...
From $351 per night (USD)
Expedia

Search Your Destination Now!

South Woods Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 202 Rentals