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From $387 per night (USD)
VRBO
Cozy recently renovated cottage on private 2+ acers of wooded paradise.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to your perfect Cape Cod retreat! Nestled in the heart of Brewster, our intimate two-bedroom cottage offers a co ...
From $387 per night (USD)
VRBO
From $317 per night (USD)
VRBO
This light and airy, street-level condo is located in Chilton Village. One bedroom Two bathrooms!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Chilton Village of the prestigious Ocean Edge Resort in Brewster near Cape Cod Bay, come enjoy your stay at t ...
From $317 per night (USD)
VRBO
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VRBO
Spacious and private home, close to four beaches and Brewster General Store
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
This renovated and newly furnished home with central air and hardwood floors throughout offers plenty of gathering space ...
Click For Pricing
VRBO
From $378 per night (USD)
Expedia
Family Friendly Home on Cobbs Pond and 100 yards from Cape Cod Bay in Brewster!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your vacation on a private setting in Brewster! Step inside a Cape Cod Saltbox that is great for a family. En ...
From $378 per night (USD)
Expedia
From $414 per night (USD)
VRBO
Short drive to town and popular beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 15578 - The Salty Hare: Short drive to town and popular beaches! The Space: Truly in the heart of Orleans and ...
From $414 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Updated Howland Village end unit
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Howland Circle, your charming retreat in Brewster, MA! This cozy 2-bedroom, 2-bathroom home offers a perfect ...
From $339 per night (USD)
VRBO
From $819 per night (USD)
VRBO
Modern A-Frame cottage with Pool set on a Horse Farm. 5 minutes from the beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful and pool and deck area just steps outside the front door. Outdoor dining are a and grill are perfect for lunch ...
From $819 per night (USD)
VRBO
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Expedia
Walking distance to Orleans, stores and baseball games! Close to bay and ocean!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Stop searching for a cute place in Orleans that's close to everything, dog friendly, and meets your budget. You're alre ...
Click For Pricing
Expedia
From $1454 per night (USD)
VRBO
Paines Creek Beach 496-B Custom, Upscale, Taste & Style - Brewster
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This property is professionally managed by Pretty Picky Properties Custom, Upscale, Taste & Style - Paines Creek Beach ...
From $1454 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Bright & Cozy with Patio, Grill and near the Beach & Golf
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Peaceful and spacious guesthouse in Brewster - minutes from Wequassett Resort, beaches, golfing & more. This space is co ...
From $257 per night (USD)
Expedia
$Cottage near bay beach- 1 Bd\/1Ba$
From $113 per night (USD)
VRBO
Cottage near bay beach- 1 Bd\/1Ba
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Condo Duplex only 2/10 of a mile to Paines Creek Beach on Cape Cod Bay great for sun-sets. 1 bedroom w/ wall A/C, one ba ...
From $113 per night (USD)
VRBO
From $373 per night (USD)
VRBO
Welcome to this lofty Ocean Edge two bedroom, two bath townhouse!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautiful and Spacious Ocean Edge Townhome! Welcome to this lofty Ocean Edge two bedroom, two bath townhouse! This beau ...
From $373 per night (USD)
VRBO
From $283 per night (USD)
VRBO
Perfect on Long Pond
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
<p>A short distance from ice skating, cross-country skiing, and more, this pet-friendly vacation home lets you experienc ...
From $283 per night (USD)
VRBO
From $756 per night (USD)
VRBO
Charming 4 BR house with AC and WiFi and outdoor shower in enchanting Harwich
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Stay comfortably in Harwich at this 4-bedroom house with deeded rights to Long Pond. This fabulous property offers a pea ...
From $756 per night (USD)
VRBO
From $332 per night (USD)
VRBO
Sheep’s Pond Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Don't wait to rent this adorable 3 bedroom home is located in the desirable Sheep Pond Estates in Brewster with Deeded r ...
From $332 per night (USD)
VRBO
$Private house near Long Pond and trails with kayaks, bikes, W\/D, and AC$
From $579 per night (USD)
Expedia
Private house near Long Pond and trails with kayaks, bikes, W\/D, and AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Quiet Long Pond Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $579 per night (USD)
Expedia
From $2421 per night (USD)
VRBO
6-bedroom, Multi-building, Private Compound with Pool in Hawksnest State Forest
Bedrooms:
6
Bathrooms:
6
Sleeps:
20
Away from the hustle & bustle of the Summer and Holiday crowds, this private estate in Harwich with a 5-bedroom main hou ...
From $2421 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Charming 3-bedroom house in marvelous Dennis with WiFi, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unwind in Dennis at this lovely house. Nestled in a charming neighborhood, this superb property offers a cozy retreat fo ...
From $470 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Renovated Cape Cod Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled on a quiet cul-de-sac close to beaches, come enjoy everything the Cape as to offer. Step inside, and be greeted ...
From $511 per night (USD)
VRBO
From $529 per night (USD)
Expedia
Cape Cottage, water views, 2bdrms, 1bth, screened porch, window AC units, steps to beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
2 Bedroom - 1 Baths - Sleeps 5 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $529 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Brewster Bay Side Cottage | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Sweet Brewster cottage is just 1/10th of a mile to Halliday Acres private bay beach via quiet neighborhood street. Main ...
From $436 per night (USD)
VRBO
From $675 per night (USD)
Expedia
A Quintessential Beach Cottage | 4 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This quintessential beach cottage has views of Cape Cod Bay from the front yard. Gorgeous vacation home just .1 mile to ...
From $675 per night (USD)
Expedia
From $710 per night (USD)
VRBO
Waterfront on Long Pond | 2 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Waterfront on Black Pond and Long Pond! Two bedrooms plus sleeping loft cottage. Inside you will find the charm of Cape ...
From $710 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Stunning Cape Home Near Chatham
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This pet & family friendly newly renovated home in the heart of the Cape has 3 bedrooms, 2.5 baths, and sleeps 8, making ...
From $569 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Pet Friendly, Sleeps 4, Huge Back Yard, Skaket Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 Bedroom - 1.5 Bathrooms - Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $377 per night (USD)
VRBO
From $893 per night (USD)
VRBO
Cozy 3-bedroom building in gorgeous Dennis with WiFi, AC
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Nestled in Dennis, this delightful building offers a tranquil and soothing retreat for guests. With 3 bedrooms, includin ...
From $893 per night (USD)
VRBO
From $549 per night (USD)
VRBO
Saint's Landing Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Minutes to the Beach and ALL Bedrooms with A/C! * * * * See end of this description for information about f ...
From $549 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Sears Point end unit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
PRIVATE ASSOCIATION BEACH & CAPE COD BAY VIEWS! * * * * See end of this description for information about f ...
From $531 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Comfortable 2-bedroom apartment in lovely Brewster Ocean Edge resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly renovated family friendly apartment overlooking golf course, close to beautiful uncrowded Brewster beaches, rail-t ...
From $452 per night (USD)
VRBO
From $714 per night (USD)
Expedia
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
It's FALL! With a deeply discounted fall price tag, come stay and enjoy the slowly changing leaves and great restaurants ...
From $714 per night (USD)
Expedia
From $758 per night (USD)
VRBO
Huge Private Beach. Fab View.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Views of the entire Cape Cod Bay. Amazing location. Gorgeous beach 360 ft long. Imagine a pristine private beach as long ...
From $758 per night (USD)
VRBO
From $847 per night (USD)
Expedia
Charming 4BR: Slps10! 9Beds! Pool & HotTub, Dog Friendly
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Sesuit Harbor Hideaway – your perfect Cape Cod getaway! This spacious 4-bedroom, 3-bathroom home offers a rel ...
From $847 per night (USD)
Expedia
$\Charming 2BR Cape Getaway with Spacious Private Backyard\ Fire Pit in a Quiet Neighborhood$
From $512 per night (USD)
VRBO
\"Charming 2BR Cape Getaway with Spacious Private Backyard\" Fire Pit in a Quiet Neighborhood
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
2 BR at 4 Russell Dr., Harwich This charming 2-bedroom home in Harwich offers a cozy retreat close to the Cape’s natura ...
From $512 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Charming 3-bedroom house in East Dennis with beautiful pool & jacuzzi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
New to VRBO!! Discover this 3-bedroom gem in East Dennis with central air and sleeps up to 8. This delightful house fea ...
From $353 per night (USD)
Expedia
From $740 per night (USD)
VRBO
Skaket Beach - Beachfront Property
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our bright, beautiful waterfront condo located directly on Skaket Beach. A perfect family vacation spot, yo ...
From $740 per night (USD)
VRBO
From $711 per night (USD)
VRBO
Time Will Tell - Incredible Brewster Residence With Breath Taking Gardens!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
"Time Will Tell" This sensational, single-level remodeled residence is a brand-new listing for 2025. Located adjacent t ...
From $711 per night (USD)
VRBO
Click For Pricing
VRBO
Charming 3 bedroom 2 bathroom private house with easy beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax with the whole family at this peaceful place to stay. Nestled in the woods, surrounded by conservation land, but c ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Charming Guest House, with Waterviews & Private Beach! Perfect for Fun Weekends!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in South Orleans, this pet-friendly sun-filled Guest House offers 2 large bedrooms and 2 full baths. Located in ...
Click For Pricing
Expedia
From $1010 per night (USD)
VRBO
Beachfront Home Offering Direct Access to Your Own Private Beach (2386)
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Escape to this beautiful beachfront home, offering direct access to your own private stretch of Cape Cod Bay beach. Perf ...
From $1010 per night (USD)
VRBO
$Pool, Hot Tub Serene Private Back Yard 1\/4 Mile to Ellis Landing Beach (2387)$
From $1713 per night (USD)
Expedia
Pool, Hot Tub Serene Private Back Yard 1\/4 Mile to Ellis Landing Beach (2387)
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to your next Cape Cod getaway! This stunning rental home is designed for relaxation and entertainment, featuring ...
From $1713 per night (USD)
Expedia
From $919 per night (USD)
VRBO
Walk to beach, Secluded and private home and backyard!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: 18840 - Walk to beach, Secluded and private home and backyard! The Space: Nestled on a hillside in Brewster, B ...
From $919 per night (USD)
VRBO
From $618 per night (USD)
Expedia
Spacious home with deck and fire pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: 18839 - The Homestead: Spacious home with deck and fire pit! The Space: Discover the charm of The Homestead, y ...
From $618 per night (USD)
Expedia
From $665 per night (USD)
VRBO
Game Room, Private Yard w Fire Pit!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 17756 - Deckside Delight: Game Room, Private Yard w Fire Pit! The Space: Welcome to Deckside Delight, a spacio ...
From $665 per night (USD)
VRBO
From $1752 per night (USD)
Expedia
5-Bedroom Vacation Haven with Pool!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Northside Retreat: 5-Bedroom Vacation Haven with Endless Outdoor Fun Welcome to your perfect Cape Cod getaway! This stu ...
From $1752 per night (USD)
Expedia
From $264 per night (USD)
VRBO
BPOPE - Just Listed! Spacious Oasis minutes to CC Rail Trail & Beaches
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
New Listing! Spacious Oasis minutes to Cape Cod Rail Trail & Beaches Escape to the serene beauty of Cape Cod with a sta ...
From $264 per night (USD)
VRBO
From $187 per night (USD)
VRBO
Landing Lane at Sea Pines
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Just Listed - Sea Pines Condo! * * * * See end of this description for information about free included acti ...
From $187 per night (USD)
VRBO
$Cozy condo with golf course view, balcony, W\/D, AC, & games$
From $327 per night (USD)
VRBO
Cozy condo with golf course view, balcony, W\/D, AC, & games
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Condo at Ocean Edge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $327 per night (USD)
VRBO
From $384 per night (USD)
Expedia
On bike path with private beach, AC, Free Linens—3 bedrooms & 2 bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Consider our cottage your home away from home while you visit Harwich with a private sandy beach on Long Pond. With 3 co ...
From $384 per night (USD)
Expedia
From $653 per night (USD)
VRBO
Seaside Breeze
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New 2025 Seaside Breeze - Charming Home in Brewster Walk to Saint's Landing Beach on Cape Cod Bay The ideal retreat wh ...
From $653 per night (USD)
VRBO
$6 Mi to Beach: Home w\/ Deck in Brewster!$
From $316 per night (USD)
Expedia
6 Mi to Beach: Home w\/ Deck in Brewster!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Peaceful Setting | Washer/Dryer | Beach Chairs & Umbrella Enjoy a memorable Cape Cod retreat with your crew at this 3-b ...
From $316 per night (USD)
Expedia
From $637 per night (USD)
VRBO
Shady Pines
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
New 2025 Shady Pines Tranquil 4 Bedroom Retreat Just Moments from Beautiful Seymour Pond in Brewster Family & dog-frie ...
From $637 per night (USD)
VRBO
From $414 per night (USD)
VRBO
Brewster Bay Breeze
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Quick Walk to the Stunning Shores of Saints Landing Beach on Cape Cod Bay! Charming three-bedroom getaway in a quiet, f ...
From $414 per night (USD)
VRBO
From $744 per night (USD)
VRBO
Sparrow's Nest
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Serene Brewster Retreat Nestled in the Pine Trees by Blueberry Pond This recently renovated home is in an amazing locati ...
From $744 per night (USD)
VRBO
From $619 per night (USD)
VRBO
Beachcomber's Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lovely 3BR Home is Just Under a Mile from Point of Rocks Beach in Brewster Great location between historic Route 6A and ...
From $619 per night (USD)
VRBO
From $3131 per night (USD)
VRBO
Ocean Edge Resort 3-bedroom 3 Bath house with AC. Premium Accomdations.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Ocean Edge Resort and Golf Club – This a private vacation home that has been completely remolded to extremely high stan ...
From $3131 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Newly Renovated Ocean Edge 2 Bedroom Condo in Fletcher Village
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Next Beach Getaway! Escape to this stunning, newly renovated 2-bedroom townhome located in the luxurious Ocean Edg ...
From $432 per night (USD)
Expedia
From $658 per night (USD)
VRBO
Welcome to your perfect summer retreat in South Orleans, MA nestled on the Cape Cod coastline!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to your perfect summer retreat in beautiful South Orleans, MA, nestled on the iconic Cape Cod coastline. This ch ...
From $658 per night (USD)
VRBO
$Icing on the Cape - Private Association Beach 0\/6 miles from your vacation home!$
From $450 per night (USD)
VRBO
Icing on the Cape - Private Association Beach 0\/6 miles from your vacation home!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
“Icing on the Cape”Beach 0/6 miles from your vacation home This delightful two story 1,328 square foot residence offers ...
From $450 per night (USD)
VRBO
From $579 per night (USD)
VRBO
My Fathers Dragon - Private Association Beach! Central Air!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
My Fathers Dragon Private Association Beach! Nestled in the peaceful and picturesque Brewster Bayside neighborhood, th ...
From $579 per night (USD)
VRBO
From $702 per night (USD)
VRBO
Beautifully Renovated Cape Cod Retreat near Pleasant Bay & Top Attractions
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*Cancellation policy at end of property description.* Nestled in the picturesque town of Harwich, Mooncusser is a beau ...
From $702 per night (USD)
VRBO
From $372 per night (USD)
VRBO
Walk to Private Bayside Beach!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: 18841 - Wave-y Days: Walk to Private Bayside Beach! The Space: Welcome to Wave-y Days, a charming vacation ret ...
From $372 per night (USD)
VRBO
From $457 per night (USD)
Expedia
2BR Brewster Family Paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Charming 2-Bedroom Vacation Home in Brewster Escape to Cape Cod and enjoy this cozy 2-bedroom vacation home located in ...
From $457 per night (USD)
Expedia
From $789 per night (USD)
VRBO
Peak Aug Weeks still avail! Sat-Sat. Brewster Farmhouse Retreat on Seymour Pond
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Surrey Farms! Unwind and recharge in our stunning 5-bedroom, 4-bathroom Cape Cod farmhouse. Surrey Farms is n ...
From $789 per night (USD)
VRBO
From $821 per night (USD)
Expedia
Pool, Half Mile to Beach!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: 17759 - Blue Lagoon: Pool, Half Mile to Beach! The Space: Perched atop a hill, this Harwich home is your gatew ...
From $821 per night (USD)
Expedia
$NEW LISTING! Newly-Renovated 4BD--Mill Pond Views, A\/C, Deck, Enclosed Outdoor Shower$
From $950 per night (USD)
VRBO
NEW LISTING! Newly-Renovated 4BD--Mill Pond Views, A\/C, Deck, Enclosed Outdoor Shower
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
NEW LISTING! VIEWS of MILL POND can be seen from almost every room. Come and enjoy your Cape Cod vacation at this beaut ...
From $950 per night (USD)
VRBO
From $838 per night (USD)
Expedia
Near Wequassett Resort and Golf Club in Harwich, overlooking a cranberry bog!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this spacious and inviting Harwich rental, perfectly situated near the Wequassett Resort and Golf Club, with b ...
From $838 per night (USD)
Expedia
From $463 per night (USD)
VRBO
Beautiful Historic Home Within a Mile of Crystal Lake
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
***NEW TO THE MARKET*** This amazing, refurbished Post and Beam Antique home is known as the Gould-Linnell House which ...
From $463 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Vacation Bliss at Ocean Edge RPAM108
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step inside to discover a bright, airy space with gleaming floors, high ceilings, and a layout that feels both inviting ...
From $368 per night (USD)
Expedia
From $312 per night (USD)
VRBO
Charming, Private Getaway with Modern Comforts and Outdoor Space (2396)
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to this charming and cozy short-term rental apartment, nestled in a peaceful neighborhood on a quiet dead-end st ...
From $312 per night (USD)
VRBO
$Modern House w\/Private Beach Access to Seymour Pond, Near Rail Trail$
From $494 per night (USD)
VRBO
Modern House w\/Private Beach Access to Seymour Pond, Near Rail Trail
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This newly renovated home offers everything you need for a memorable Cape Cod vacation. You don’t have to choose between ...
From $494 per night (USD)
VRBO
From $963 per night (USD)
VRBO
Brewster coastal charm - 4 bed home - short walk to two beaches - sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to CapeCodProperty 175, a stunning 4-bedroom home with serene views of Cape Cod Bay from the upper deck. Nestled ...
From $963 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Ocean Edge Condo - Resort Pool & Close to Beaches!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bright & spacious one bedroom, one bath, 2nd floor unit at prestigious Ocean Edge. Access to resort pool, tennis courts, ...
From $262 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Charming 4-bedroom house with AC and WiFi steps from Wequassett Resort
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Escape to your perfect Cape Cod summer with this stunning rental property located steps away from the beauty of Pleasant ...
From $840 per night (USD)
VRBO
From $844 per night (USD)
Expedia
Waterfront on Pleasant Bay!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 17711 - Island Views: Waterfront on Pleasant Bay! The Space: Wake up to sweeping views of Pleasant Bay, where ...
From $844 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Great location with Water Views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: 17710 - Captains Cottage: Great location with Water Views! The Space: Escape to the charm of Harwich, where th ...
From $563 per night (USD)
VRBO
From $353 per night (USD)
VRBO
New listing in Howland Circle at Ocean Edge Villages with Pool Access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**NEW LISTING** **POOL ACCESS** **NO SPIRAL STAIR!** * * * * See end of this description for information ab ...
From $353 per night (USD)
VRBO
From $471 per night (USD)
VRBO
Escape to this stunning Cape Cod townhome in Howland Village in Brewster!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to this stunning Ocean Edge townhome in Howland Village! This spacious rental features 2 bedrooms and 2 full bath ...
From $471 per night (USD)
VRBO
From $555 per night (USD)
VRBO
Secluded Brewster Retreat - Direct Access to Trails, 5 minutes to the Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled against 50 acres of conservation land, this Cape Cod retreat offers a serene escape with direct access to hiking ...
From $555 per night (USD)
VRBO
From $399 per night (USD)
VRBO
Bog Pond Road Beauty, close to 6A & Brewster Beaches!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Lovingly and beautifully renovated 4 bedroom, 2 full bath home with central A/C in the heart of Brewster, is the perfect ...
From $399 per night (USD)
VRBO
From $323 per night (USD)
VRBO
Point of Rocks Beach at the right price!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Only 4/10's mile to public Point of Rocks Beach on Cape Cod Bay! * * * * See end of this description for in ...
From $323 per night (USD)
VRBO
From $680 per night (USD)
VRBO
Spacious Home With Private Yard Close to Beach Abutting Conservation (2397)
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
***NEW FOR 2025*** Escape to this beautifully designed one-story home, perfectly positioned just 0.6 miles from Saints L ...
From $680 per night (USD)
VRBO
From $911 per night (USD)
Expedia
South Cottage: 2285-H Waterfront, Six Bedrooms, Free Boating Bonus!
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
This home is professionally managed by Pretty Picky Properties Waterfront, Six Bedrooms, Free Boating Bonus! NEW Listi ...
From $911 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Square Top: 661-O Spectacular Pleasant Bay Views, Free Boating Bonus!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This home is professionally managed by Pretty Picky Properties Spectacular Pleasant Bay Views, Free Boating Bonus! NEW ...
From $755 per night (USD)
VRBO
From $424 per night (USD)
VRBO
Charming home near Cape Cod Rail Trail offers comfort, convenience, and classic New England appeal.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Tucked away near the scenic Cape Cod Rail Trail, this delightful single-family home seamlessly combines comfort, conveni ...
From $424 per night (USD)
VRBO
From $681 per night (USD)
VRBO
Robinson Road Beach House
Bedrooms:
1
Bathrooms:
1
Sleeps:
10
Minutes to Private Beach! This cozy 5 bedroom, two full bathroom cottage is just off the shared private beaches on Brew ...
From $681 per night (USD)
VRBO
$BNEHJ - NEW LISTING! Howland Circle End unit with great A\/C at Ocean Edge Villages$
From $292 per night (USD)
VRBO
BNEHJ - NEW LISTING! Howland Circle End unit with great A\/C at Ocean Edge Villages
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
JUST RELISTED - NEW OWNERSHIP! **POOL PASSES NOW AVAILABLE WITH YOUR STAY** * * * * See end of this descrip ...
From $292 per night (USD)
VRBO
$3BD Main Street Retreat--A\/C, Fire Pit, Enclosed Outdoor Shower$
From $453 per night (USD)
VRBO
3BD Main Street Retreat--A\/C, Fire Pit, Enclosed Outdoor Shower
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to this lovely vacation rental in Brewster, MA! This three-bedroom, two full-bath duplex* exudes a relaxed Cap ...
From $453 per night (USD)
VRBO
From $490 per night (USD)
VRBO
Fire pit, By Long Pond + Greenland Pond, sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This newly renovated home is spotless and stylish, offering 3 bedrooms plus a pullout sleeper to comfortably sleep 8, wi ...
From $490 per night (USD)
VRBO
From $1013 per night (USD)
VRBO
Sleeps 12, Hot Tub, 5 min to Beach, Bocce Ball
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Renovated Brewster retreat, perfect for groups or families! ✓ Sleeps 12: 2+ bedroom house with loft and sunroom + 2-bed ...
From $1013 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Newly renovated Mid-Century Modern beach experience in Brewster
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy this centrally located home in Brewster that has been updated with modern amenities and beachy casual feel. Relax ...
From $351 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Cozy 1 bedroom with fenced in yard, porch and association lake beach access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to this lovely apartment in Brewster. This fabulous rental features 1 cozy bedroom with a queen bed, a well-equi ...
From $252 per night (USD)
VRBO
From $277 per night (USD)
VRBO
Grandfather's Lane charmer
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Central AC & Minutes to Beach! * * * * See end of this description for information about free included act ...
From $277 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Minutes to beautiful Saints Landing Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This unique and beautiful home located in the historic district of Brewster sits just 0.3 miles to Saint's Landing Beach ...
From $342 per night (USD)
VRBO
$3BD Herring Run Antique--A\/C, Fire Pit & Enclosed Outdoor Shower$
From $429 per night (USD)
VRBO
3BD Herring Run Antique--A\/C, Fire Pit & Enclosed Outdoor Shower
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Brewster Historic District Antique & Dog Friendly! * * * * See end of this description for information abou ...
From $429 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Pineland Park - Private Association Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Private Association Beach access!! Brewster Flats * * * * See end of this description for information about ...
From $452 per night (USD)
VRBO
From $928 per night (USD)
Expedia
Peaceful and private vacation rental on the pond!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Peaceful and private vacation rental on the pond! This charming 3 bedroom (king, queen, full), 3 bathroom home in Orlean ...
From $928 per night (USD)
Expedia
From $412 per night (USD)
VRBO
SHORT WALK TO PRIVATE ASSOCIATION BEACH!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Moments to Private Association Beach! * * * * See end of this description for information about free inclu ...
From $412 per night (USD)
VRBO
From $592 per night (USD)
VRBO
BREWSTER PARK PRIVATE BEACH ASSOCIATION, BOAT MOORING AMENITIES GALORE!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Brewster Park Vacation Rental * * * * See end of this description for information about free included activ ...
From $592 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Ocean Edge with GOLF and Pool Passes available!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Ocean Edge end unit with Golf, Central A/C and Pool Passes available! **LINENS INCLUDED!** * * * * See end ...
From $465 per night (USD)
VRBO
From $813 per night (USD)
VRBO
Bayside Beach Beauty!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayside Beach Beauty! * * * * See end of this description for information about free included activities, K ...
From $813 per night (USD)
VRBO

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