1149+ Treehouses, Forest Homes, Cabin Rentals, and Private Nature Retreats in Oak Square |
Tree House Rentals in Oak Square
Apartment
- Boston
- ·
- Observatory Hill
- 0.14 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
1175 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $287/Night
7 Nights - US $2,012
Apartment
- Boston
- ·
- Cleveland Circle
- 0.10 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
495.14 ft²
Pet Friendly- Parking
Air Conditioner
Internet
US $89/Night
7 Nights - US $623
Hotel
9.2Exceptional
(1001 Reviews)
1 Bath
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
US $209/Night
7 Nights - US $1,462
Apartment
- Boston
- ·
- North Brookline
- 0.19 mi to center
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $406/Night
7 Nights - US $2,841
Apartment
- Boston
- ·
- Coolidge Corner South Side
- 0.25 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
4843.76 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $237/Night
7 Nights - US $1,659
New
Apartment
- Boston
- ·
- North Brookline
- 0.28 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $355/Night
7 Nights - US $2,483
New
Apartment
- Boston
- ·
- St. Elizabeth's
- 0.27 mi to center
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $313/Night
7 Nights - US $2,189
Condo
- Boston
- ·
- Newtonville
- 0.55 mi to center
10.0Exceptional
(32 Reviews)
3 Bedrooms
1 Bath
5 Guests
1100 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $306/Night
7 Nights - US $2,142
Apartment
- Boston
- ·
- St. Elizabeth's
- 0.04 mi to center
10.0Exceptional
(29 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $403/Night
7 Nights - US $2,820
Luxury Tree House Rentals in Oak Square
Over 1140+ Luxury Tree House Rentals in or Near Oak Square
US $9,605/Night
7 Nights - US $67,236
US $9,605/Night
7 Nights - US $67,236
US $9,605/Night
7 Nights - US $67,236
Apartment
- Boston
- ·
- Lower Allston
- 0.45 mi to center
8.9Fabulous
(36 Reviews)
14 Bedrooms
1 Bath
3 Guests
602.78 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
US $7,670/Night
7 Nights - US $53,690
House
4 Bedrooms
2 Baths
8 Guests
- Parking
- Internet
Child Friendly
Security/Safety
US $4,479/Night
7 Nights - US $31,352
Apartment
- Boston
- ·
- Cambridgeport
- 0.23 mi to center
10.0Exceptional
(1 Review)
8 Bedrooms
3 Baths
24 Guests
2002.09 ft²
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Parking
US $4,098/Night
7 Nights - US $28,686
US $2,928/Night
7 Nights - US $20,495
US $2,636/Night
7 Nights - US $18,453
US $2,497/Night
7 Nights - US $17,478
Top-Rated Treehouses with a Pool in Oak Square
Over 113+ Top-Rated Private Treehouses with a Pool in or Near Oak Square
House
- Boston
- ·
- Thompsonville
- 0.22 mi to center
10.0Exceptional
(11 Reviews)
3 Bedrooms
3 Baths
8 Guests
4000 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $830/Night
7 Nights - US $5,809
Condo
- Boston
- ·
- Cleveland Circle
- 0.29 mi to center
9.8Exceptional
(89 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $168/Night
7 Nights - US $1,175
Hotel
9.0Exceptional
(2 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $293/Night
7 Nights - US $2,053
Hotel
8.9Fabulous
(224 Reviews)
6 Baths
482.22 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $398/Night
7 Nights - US $2,787
Hotel
8.6Fabulous
(668 Reviews)
1 Bath
440.42 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $371/Night
7 Nights - US $2,600
Hotel
8.5Fabulous
(231 Reviews)
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $375/Night
7 Nights - US $2,627
Hotel
- Boston
- ·
- Newton Corner
- 0.47 mi to center
8.4Excellent
(2850 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $124/Night
7 Nights - US $868
Hotel
8.3Excellent
(538 Reviews)
1 Bath
247.57 ft²
- Private Pool
- Pool
- Pet Friendly
- Parking
US $529/Night
7 Nights - US $3,700
Apartment
- Boston
- ·
- Cleveland Circle
- 0.36 mi to center
8.0Excellent
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
624.31 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
US $160/Night
7 Nights - US $1,120
Pet-Friendly Treehouses in Oak Square
Over 410+ Pet-Friendly Private Treehouses in or Near Oak Square
Apartment
- Boston
- ·
- Jamaica Plain
- 1.33 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $153/Night
7 Nights - US $1,072
Apartment
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
8 Guests
914.93 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $351/Night
7 Nights - US $2,454
Apartment
6.4Good
(48 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $276/Night
7 Nights - US $1,932
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $226/Night
7 Nights - US $1,579
House
9.8Exceptional
(21 Reviews)
5 Bedrooms
2 Baths
8 Guests
1700.7 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $843/Night
7 Nights - US $5,904
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.47 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $510/Night
7 Nights - US $3,572
Apartment
9.6Exceptional
(18 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $456/Night
7 Nights - US $3,190
Apartment
- Boston
- ·
- West Cambridge
- 0.47 mi to center
9.4Exceptional
(125 Reviews)
1 Bedroom
1 Bath
4 Guests
330 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $195/Night
7 Nights - US $1,366
Apartment
9.4Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $326/Night
7 Nights - US $2,284
Large Private Treehouses in Oak Square
Over 91+ Large Treehouses in or Near Oak Square for Groups and Families
Condo
- Boston
- ·
- Griggs Park
- 0.02 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
4 Baths
10 Guests
1001 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,195/Night
7 Nights - US $8,367
Apartment
9.7Exceptional
(3 Reviews)
12 Bedrooms
8 Baths
24 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $730/Night
7 Nights - US $5,110
Apartment
8.0Excellent
(2 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Kitchen
- Internet
- Child Friendly
US $528/Night
7 Nights - US $3,698
Apartment
- Boston
- ·
- Griggs Park
- 0.03 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,450/Night
7 Nights - US $10,149
Bed & Breakfast
9.4Exceptional
(102 Reviews)
8 Bedrooms
13 Baths
18 Guests
156.07 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Air Conditioner
US $308/Night
7 Nights - US $2,156
Apartment
- Boston
- ·
- High Street Hill
- 0.18 mi to center
9.4Exceptional
(43 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $780/Night
7 Nights - US $5,459
Apartment
- Boston
- ·
- Griggs Park
- 0.15 mi to center
4 Bedrooms
4 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,413/Night
7 Nights - US $9,891
House
- Boston
- ·
- High Street Hill
- 0.14 mi to center
6 Bedrooms
2 Baths
14 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,362/Night
7 Nights - US $9,534
House
- Boston
- ·
- Fenway–Kenmore
- 0.52 mi to center
10.0Exceptional
(80 Reviews)
7 Bedrooms
3 Baths
14 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,782/Night
7 Nights - US $12,472
Wheelchair Accessible Holiday Homes in Oak Square
Over 449+ Wheelchair Accessible Treehouses and Holiday Homes in or Near Oak Square
Apartment
- Boston
- ·
- Mid-Cambridge
- 0.22 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $743/Night
7 Nights - US $5,198
Bed & Breakfast
- Boston
- ·
- Mid-Cambridge
- 0.24 mi to center
8.6Fabulous
(519 Reviews)
21 Bedrooms
5 Baths
11 Guests
109.79 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Air Conditioner
US $195/Night
7 Nights - US $1,365
Hotel
- Boston
- ·
- Cambridgeport
- 0.38 mi to center
8.8Fabulous
(1007 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $213/Night
7 Nights - US $1,494
Apartment
- Boston
- ·
- Cleveland Circle
- 0.05 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $164/Night
7 Nights - US $1,151
Apartment
- Boston
- ·
- North Brookline
- 0.32 mi to center
7.8Very Good
(46 Reviews)
1 Bedroom
1 Bath
2 Guests
301.39 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $481/Night
7 Nights - US $3,367
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.38 mi to center
1 Bedroom
1 Bath
2 Guests
709 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $357/Night
7 Nights - US $2,499
Apartment
- Boston
- ·
- Central Square
- 0.21 mi to center
2 Bedrooms
2 Baths
4 Guests
1484 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $354/Night
7 Nights - US $2,478
Apartment
- Boston
- ·
- Cambridgeport
- 0.34 mi to center
1 Bedroom
1 Bath
2 Guests
779 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $342/Night
7 Nights - US $2,394
Apartment
- Boston
- ·
- Cambridgeport
- 0.34 mi to center
1 Bedroom
1 Bath
2 Guests
786 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $337/Night
7 Nights - US $2,359
Oak Square Treehouses, Airbnb and Holiday Homes Under $200
Over 288+ Oak Square Private Treehouses, Airbnb and Holiday Homes Under $200
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $175/Night
7 Nights - US $1,224
Apartment
9.1Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
4 Guests
904.17 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $157/Night
7 Nights - US $1,099
US $146/Night
7 Nights - US $1,021
Apartment
- Boston
- ·
- Newton Highlands
- 0.23 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $140/Night
7 Nights - US $980
Apartment
- Boston
- ·
- Emerson Gardens
- 0.16 mi to center
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $132/Night
7 Nights - US $924
New
Apartment
9.4Exceptional
(40 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $199/Night
7 Nights - US $1,394
House
- Boston
- ·
- Neighborhood Nine
- 0.12 mi to center
6.0Good
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $165/Night
7 Nights - US $1,154
Apartment
6.0Good
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $188/Night
7 Nights - US $1,319
Apartment
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $198/Night
7 Nights - US $1,386
Instantly Bookable Treehouse Rentals in Oak Square
Over 650+ Instantly Bookable Private Treehouses in or Near Oak Square
Apartment
- Boston
- ·
- West Cambridge
- 0.57 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $653/Night
7 Nights - US $4,573
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $89/Night
7 Nights - US $626
Apartment
- Boston
- ·
- Fenway–Kenmore
- 0.48 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $835/Night
7 Nights - US $5,842
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
5 Guests
650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $640/Night
7 Nights - US $4,478
Condo
- Boston
- ·
- Neighborhood Nine
- 0.31 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $409/Night
7 Nights - US $2,864
Apartment
- Boston
- ·
- St. Elizabeth's
- 0.17 mi to center
9.8Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
1400 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $440/Night
7 Nights - US $3,079
Apartment
9.6Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $360/Night
7 Nights - US $2,522
Apartment
- Boston
- ·
- Central Square
- 0.20 mi to center
9.4Exceptional
(87 Reviews)
1 Bedroom
1 Bath
3 Guests
300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $339/Night
7 Nights - US $2,371
House
- Boston
- ·
- West Cambridge
- 0.17 mi to center
9.4Exceptional
(22 Reviews)
2 Bedrooms
1 Bath
6 Guests
818 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $448/Night
7 Nights - US $3,139
Book a Last Minute Place to Stay in Oak Square
About Oak Square Treehouse Rentals
Explore more than 1149 treehouses in Oak Square. From luxurious treetop retreats to cozy forest homes, cabins and off-grid properties, each offers premium amenities designed for families, groups, and adventurers. Enjoy exceptional comfort and a one-of-a-kind nature experience with these incredible accommodations. Perfect for tranquil escapes, adventurous retreats, or nature-inspired getaways, these treehouses provide style and comfort in Oak Square.
Looking for last-minute deals or the best offers on treehouses, cozy forest homes, cabins and off-grid properties? Treehouse Rentals makes it easy to compare options in Oak Square. Choose from spacious family-friendly stays, charming woodland escapes, or luxurious treetop getaways tailored for ultimate relaxation and adventure
Find spacious family-friendly accommodations, cozy forest homes, or luxurious treetop stays—all designed for maximum comfort and convenience during your visit.On average, treehouses in Oak Square offer approximately 579.64 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning natural surroundings.
The average nightly rate for treehouses in Oak Square typically ranges around US $433.
Treehouse Rentals offers a secure and convenient platform to compare and book the best treehouses in Oak Square. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in nature with us.
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Top Treehouse Accommodation Types in Oak Square
| Type | Count |
|---|---|
| Holiday Apartments | 743 |
| Vacation Homes | 212 |
| Cottages | 1 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Oak Square
★ Pro Tip: Treehouse Rentals simplifies your search for the best treehouse accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore treehouses, cozy cabins, secluded forest homes and off-grid properties. Filter by availability, pricing, cancellation options, and amenities to discover the ideal treehouse getaway in Oak Square.
Weather in Oak Square, MA
View the weather forecast for Oak Square before booking your Oak Square Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Oak Square?
What are the top treehouse rentals in Oak Square?
Looking for a place to stay in Oak Square? Explore these highly-rated treehouses for a one-of-a-kind retreat surrounded by nature:
- "The Treehouse" : Elegant living near Harvard
- Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
- UltraLuxe Apt in Boston Brownstone in Prime Area
- The Inn at Newton Highlands, Suite 2, Apartment-Hotel
- Premium Furnished 2B 1.5B Home Monthly Stay in Newton
- Remodeled Spacious Apartment in Perfect Location
- Clean, Spacious and Located Steps Away From the MBTA!
- Spacious 2 bedroom home in Harvard Square with permitted free on street parking
- Tranquil Renovated 3BR Allston Condo + Parking , Close to Harvard/BU/BC/MIT!
- Sunny 3BR house 10 min walk from Harvard Square
How many treehouses with private pools are available in Oak Square?
Find exceptional treehouses with private pools near Oak Square on Treehouse Rentals. Relax in serene treetop accommodations with exclusive pool access and picturesque nature views. Whether it's a spacious treehouse or a secluded forest retreat, these properties provide the ideal mix of luxury and adventure.
- Oversized 1Bed w/Outdoor Pool & Elevator
- Four Points by Sheraton Boston Newton
- Sun-filled Unit, Elevator, Pool, Boston College
- Courtyard by Marriott Boston Brookline
What are the top-rated treehouses in Oak Square for family stays?
Searching for a family-friendly treehouse in Oak Square? Discover these top-rated options, each loved by families and groups who have stayed in Oak Square:
- 10 mins to Boston, 2 Bedroom, 2 Bathroom, Kitchen, 1,300 SF Private Living Space
- Cambridge Base Steps to Porter Square
- Ginkgo House on Harvard
How many treehouses are available in Oak Square?
Treehouse Rentals, as of 2026, features over 1149 unique treehouse, cabins and forest homes in Oak Square. Choose from treetop hideaways, eco-friendly lodges, and off-grid properties, with new options added frequently.
By 2026, Treehouse Rentals has curated over 1149 stunning properties in Oak Square, sourced from trusted platforms. Plan your nature-inspired getaway now.
For 2026, Treehouse Rentals provides access to over 1149 premier accommodations in Oak Square. Find your ideal escape among the treetops today.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Allston Vacation Rentals in Boston, Massachusetts | 98 |
| Brighton Vacation Rentals in Boston, Massachusetts | 65 |
| Cleveland Circle Vacation Rentals in Boston, Massachusetts | 50 |
| Commonwealth Vacation Rentals in Boston, Massachusetts | 26 |
| St. Elizabeth's Vacation Rentals in Boston, Massachusetts | 26 |
| Newton Corner Vacation Rentals in Boston, Massachusetts | 551 |
| Hunnewell Hill Vacation Rentals in Boston, Massachusetts | 693 |
People Also Ask
Finding the best prices in Oak Square
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