
Three Oaks Rentals

- From $283 per night (USD)
VRBO
The Sycamore Cottage - 2 BR & 1.5 Bath - Hot Tub - Steps to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
The Sycamore Cottage is a 2 bedroom 1.5 bathroom one story single family home. The single floor design hosts two queen s ...
From $283 per night (USD)VRBO
- From $322 per night (USD)
Expedia
Cottage In The Heart Of Harbor Country - Steps From Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located steps from the Village of Three Oaks, guests can walk to Vickers Theatre, Featherbone Factory, Acorn Theatre, Fr ...
From $322 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Stay in downtown Three Oaks overlooking the main street!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A gem among area lodging options, the Bistro Apt is a beautifully renovated downtown residence that overlooks Elm Street ...
From $270 per night (USD)VRBO
- From $287 per night (USD)
Expedia
The Getaway - Three Oaks Cottage 3 BR 1.5 Bath - Week Stay Discount
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Getaway. A few minutes ...
From $287 per night (USD)Expedia
- From $293 per night (USD)
VRBO
In the Heart of Three Oaks - Steps to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully remodeled, repainted and deep cleaned. All new beds, linens and furniture. One block from downtown Three Oaks, Ant ...
From $293 per night (USD)VRBO
- From $397 per night (USD)
Expedia
Walk to Journeyman Renovated Spacious Victorian House, Beautiful Vintage Details
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Beautiful renovated stately home, one of the original founder's homes of Three Oaks! Just around the corner from the Jou ...
From $397 per night (USD)Expedia
- From $407 per night (USD)
VRBO
Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
HIGHLIGHTS: ✔ Designer rehab in 2022 ✔ Sleeps 8 ✔ Outdoor firepit ✔ Relaxing back porch ✔ 5 min walk to Journeyman ✔ Eas ...
From $407 per night (USD)VRBO
- From $340 per night (USD)
Expedia
3 bed\/2 bath designer home 100 steps to Journeyman! Just 30 mins to Notre Dame!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Situated on one of the largest private park-like settings in the village and just a stone's throw from Journeyman Distil ...
From $340 per night (USD)Expedia
- From $187 per night (USD)
VRBO
Charming\/Cozy 2 BR 1 Bath steps from downtown.\n\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming 2 BR/1Bth bungalow is located in the middle of Harbor Country and only 1 block from all the cute shops/res ...
From $187 per night (USD)VRBO
- From $484 per night (USD)
Expedia
Sycamore Suites-Entire Home Steps from Journeyman
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 10
Summary: Welcome to The Sycamore Suites, the 10 guest home just steps from Journeyman Distillery and everything that bea ...
From $484 per night (USD)Expedia
- From $2475 per night (USD)
VRBO
2025\/2026 Open! - Colossal Loft in Three Oaks. 3 Night Summer Minimum
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 18
5 Bedrooms, 4.5 Baths, Sleeps 18 Calendar OPEN through 2026!! Three Night Summer Min! Located in the historic Featherb ...
From $2475 per night (USD)VRBO
- From $303 per night (USD)
Expedia
2025\/2026 Open! Three Oaks Charmer W\/ Two Night Summer Minimum
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedrooms, 1 Bathroom, Sleeps 4 Two Night Summer Minimum! CALENDAR OPEN 2025 and 2026! Located just steps from down ...
From $303 per night (USD)Expedia
- From $414 per night (USD)
VRBO
Our Beautiful Home Away From Home For Your Stay
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our home had an extensive ten month renovation top to bottom inside and out, everything in our home is brand new includ ...
From $414 per night (USD)VRBO
- Click For Pricing
Expedia
The super comfy Buck!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Buck is a 3 bedroom, 1 bath single story home. The master bedroom has a queen size bed. Two additional bedrooms bo ...
Click For PricingExpedia
- From $648 per night (USD)
VRBO
The Hickory House - Walk to Downtown Three Oaks - Week Stay Discount
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 12
Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Hickory House. Less tha ...
From $648 per night (USD)VRBO
- From $804 per night (USD)
VRBO
Sycamore Guesthouse, steps to Journeyman Distillery!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Sycamore Guesthouse, where contemporary furnishings meet within a restored 1880's Victorian home with all modern conven ...
From $804 per night (USD)VRBO
- From $340 per night (USD)
VRBO
The Heartwood House<3 : Dwntwn Three Oaks, 2BR\/2BA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Newly renovated 1920's Bungalow loaded with character. Spacious interior with a mix of modern and vintage furnishings th ...
From $340 per night (USD)VRBO
- From $858 per night (USD)
VRBO
Luxury Accommodations for 14 Guests Near Journeyman Distillery and More!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
“Ashmoor” was originally built circa 1905 at 6 East Ash Street, where it remained in the McGawn family through the early ...
From $858 per night (USD)VRBO
- From $296 per night (USD)
VRBO
Charming, cozy and 5 star home STEPS to Journeyman & Acorn Theatre!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Oaks - a Special Place! STEPS AWAY from the Journeyman Distillery, Acorn Theatre and only a block away t ...
From $296 per night (USD)VRBO
- From $253 per night (USD)
Expedia
Backyard Oasis w Downtown Walkability, Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Backyard Oasis – A charming, well-maintained home offered by Third Coast Vacations. Location: Quiet side street in down ...
From $253 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Juniper Presents: The Fourth Oak, Steps to, Journeyman, Downtown & Parks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This sweet rental near Lake Michigan beaches, downtown Three Oaks, and countless vacation activities offers comfort and ...
From $500 per night (USD)VRBO
- From $272 per night (USD)
Expedia
Oaks Bungalow\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Newly renovated the Oaks Bungalow offers a modern mix aesthetic so comfortable you will feel right @ home. Located in a ...
From $272 per night (USD)Expedia
- From $379 per night (USD)
VRBO
Three Oaks Home Close To Everything! Two Night Summer Min!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedrooms, 1 Bathroom, Sleeps 6 2025 Calendar OPEN! Two Night Summer Min! Located in the charming town of Three Oaks, ...
From $379 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Three Oaks Multi Unit (2 Night Summer Min)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedrooms, 1 Bathroom, Sleeps 4 2025 Calendar OPEN! Two Night Summer Min! Located in the charming town of Three Oaks, ...
From $268 per night (USD)Expedia
- From $188 per night (USD)
VRBO
Three Oaks Unit Steps To Downtown! 2 Night Summer Min!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
1 Bedroom, 1 Bathroom, Sleeps 2 2025 Calendar OPEN! Two Night Summer Min! Located in the charming town of Three Oaks, ...
From $188 per night (USD)VRBO
- From $1622 per night (USD)
Expedia
The Parish House! 6 bdrm, 8 bath home in the heart of the Village of Three Oaks!
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to the Parish House, nestled in the Village of Three Oaks and within walking distance of all restaurants, weddin ...
From $1622 per night (USD)Expedia
- From $206 per night (USD)
VRBO
Quill and Cask, comfy home steps from Journeyman.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a getaway with friends or family in this cozy home located in Three Oaks, Michigan just steps from the Journeyman ...
From $206 per night (USD)VRBO
- From $381 per night (USD)
Expedia
Irish Spring in Three Oaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A beautiful 1870s home that has been made exceptionally stylish and basically brand new! Our home has been professionall ...
From $381 per night (USD)Expedia
- From $212 per night (USD)
VRBO
4 Guest Apt Steps to Journeyman & Downtown 3 Oaks
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Summary: Welcome to The Sycamore Suites Unit A, the 2-bedroom 2-bathroom unit located just steps from Journeyman Distill ...
From $212 per night (USD)VRBO
- From $286 per night (USD)
Expedia
6-Guest Apt Steps to Journeyman & Downtown 3 Oaks!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Welcome to The Sycamore Suites Unit B, the 3-bedroom 2-bathroom unit located just steps from Journeyman Distill ...
From $286 per night (USD)Expedia
- From $346 per night (USD)
VRBO
Fully Renovated Mid-Century Modern Bank in the Heart of Three Oaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Mid-Century Modern Gem – Perfect for Gatherings Step into a unique short-term rental experience at this newly renovated ...
From $346 per night (USD)VRBO
- From $478 per night (USD)
Expedia
Renovated Victorian Home with Private Garden & Fire Pit!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
About this space Tucked away on a vast 8442 sq. ft. lot, this revamped 3-bed Colonial style house is your perfect hideaw ...
From $478 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town! \n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A romantic getaway in a private wooded setting in the charming Village of Three Oaks sits in a secluded corner of a larg ...
From $175 per night (USD)VRBO
- From $266 per night (USD)
Expedia
Three Oaks Home w\/ Guest House - 8 Mi to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Gather around the fire pit and have a cookout on the deck when you retreat with family or friends to this charming home ...
From $266 per night (USD)Expedia
- From $290 per night (USD)
VRBO
Three Oaks, Michigan. Beautiful Southwestern Michigan
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located 0.8 miles from the center of Village of Three Oaks, guests can walk to Vickers Theatre (0.8mi), Featherbone Fact ...
From $290 per night (USD)VRBO
- From $307 per night (USD)
Expedia
Elm St Retreat - 3 Min walk to Downtown Three Oaks
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Welcome to The Elm Street Retreat in beautiful Three Oaks, Michigan! Fully updated with a large backyard, you w ...
From $307 per night (USD)Expedia
- From $174 per night (USD)
VRBO
2 BD steps to downtown, 1 block to journeyman & the acorn
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Sycamore Street Apartment, a thoughtfully designed space in the heart of Three Oaks, MI. This apartment i ...
From $174 per night (USD)VRBO
- From $245 per night (USD)
Expedia
Quaint, budget-friendly home walking distance to town with grill - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Nook Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $245 per night (USD)Expedia
- From $284 per night (USD)
VRBO
(Two Night Minimum!) Three Oaks Charmer Right In Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedrooms, 1 Bathroom, Sleeps 4 Located right in the heart of downtown Three Oaks, welcome to Artist Skylight Retreat! ...
From $284 per night (USD)VRBO
- Click For Pricing
Expedia
Welcome home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
I’d love to share my family home with you, yours and friends. It comes baby equipped and feel free to snack on treats, m ...
Click For PricingExpedia
- From $623 per night (USD)
VRBO
Juniper Presents: Elegant & Cozy Guesthouse w\/ Hot Tub + Firepit, Walk to Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pet-friendly 3BR/2BA gem minutes from Lake Michigan beaches and Harbor Country amenities! Rich wood floors and chic furn ...
From $623 per night (USD)VRBO
- From $292 per night (USD)
VRBO
Charming Three Oaks Cottage - dog friendly with a fenced yard and hot tub!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Get away in style to the Cherry Tree Cottage located in a quiet corner of Three Oaks. You’ll enjoy a private home with a ...
From $292 per night (USD)VRBO
- From $287 per night (USD)
VRBO
Poplar Place - 3 BR - Hot Tub - Steps from Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, Poplar Place. A few minutes ...
From $287 per night (USD)VRBO
- Click For Pricing
Expedia
New Home walking distance from charming downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This brand new constructed home features modern clean designs with all the comfort of a charming quiet getaway! 3 bedroo ...
Click For PricingExpedia
- From $363 per night (USD)
VRBO
Ash & Elm • Your Home Away From Home!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Ash & Elm, your home away from home in beautiful Three Oaks, Michigan! Fully updated with a large ba ...
From $363 per night (USD)VRBO
- From $344 per night (USD)
Expedia
Family Home with Porch & Deck, Private Hot Tub, Firepit, & Fast WiFi - 1 Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Three Oaks Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $344 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Perfect for groups! Walk to Journeyman\/downtown Three Oaks
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Elm St Charmer- Enjoy the detail and character of a 1910 farmhouse with high-end upgrades in this inviting 5 bed/3 bath ...
From $366 per night (USD)VRBO
- From $722 per night (USD)
Expedia
Charming 4-bedroom house with WiFi and AC in gorgeous Three Oaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 5
Your cozy getaway awaits in Three Oaks at this phenomenal house. With 4 bedrooms, including 1 bunk bed, there's plenty o ...
From $722 per night (USD)Expedia
- From $506 per night (USD)
VRBO
NANTUCKET OASIS!\nCharming 4-bedroom house in Three Oaks with AC and WiFi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your serene getaway awaits at this 4-bedroom house in Three Oaks. With a king bed and queen bed, guests will find the pe ...
From $506 per night (USD)VRBO
- From $662 per night (USD)
VRBO
Three Oaks Getaway- 5 BR 2.5 BA- 3 Mins to Downtown- Week Stay Discount
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Three Oaks Getaway. A s ...
From $662 per night (USD)VRBO
- From $866 per night (USD)
VRBO
Journeyman Distillery Farmhouse in Three Oaks! Three Night Summer Minimum!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
3 Bedrooms (and a loft), 3 Bathrooms, Sleeps 10 Three Night Summer Minimum OPEN through 2025!! Country Chic located ...
From $866 per night (USD)VRBO
- From $244 per night (USD)
VRBO
Charming 2-bedroom cottage steps to downtown Three Oaks, short drive to beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your home away from home in Three Oaks with 2 bedrooms and pull out bed to sleep 6 for larger families. This cozy cottag ...
From $244 per night (USD)VRBO
- From $423 per night (USD)
VRBO
Three Oaks Home With Three Night Summer Min!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedrooms, 1.5 Bathroom, Sleeps 8 Three Night Summer Minimum! Just steps away from Journeyman Distillery and lovely d ...
From $423 per night (USD)VRBO
- From $342 per night (USD)
Expedia
Featherbone Farmhouse- Comfy Gem 1 Block to Town. Perfect for families & groups!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Featherbone Farmhouse! This elegant & comfy home was recently fully refreshed and refurnished, designed for ...
From $342 per night (USD)Expedia