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Brookline Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Brookline vacation rentals

A garden with a wooden pergola, purple flowers, and a river view.

1. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is ￥22,589
￥43,396 total
includes taxes & fees
Oct 27 - Oct 28
Family Friendly Hilltop House In Putney Vermont
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

2. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is ￥25,099
￥44,626 total
includes taxes & fees
Nov 3 - Nov 4
Wellness Getaway with a Personal Sauna, and Private River Beach!
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

3. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (20 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is ￥14,118
￥24,680 total
includes taxes & fees
Oct 27 - Oct 28
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

4. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is ￥11,295
￥16,309 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Vermont Tiny Home Get Away
A wooden house with a porch lit by string lights, surrounded by snow.

5. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
The price is ￥18,373
￥69,290 total
includes taxes & fees
Nov 9 - Nov 10
Chalet Mount Snow/Stratton Skiing/hiking
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

6. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is ￥10,504
￥50,868 total
includes taxes & fees
Nov 2 - Nov 3
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A red house with a covered porch and a chimney.

7. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (174 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is ￥26,668
￥57,452 total
includes taxes & fees
Oct 27 - Oct 28
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

8. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is ￥24,158
￥30,844 total
includes taxes & fees
Oct 28 - Oct 29
The Eagles Wing at The CHM - Private Apartment
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

9. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is ￥21,883
￥43,166 total
includes taxes & fees
Oct 28 - Oct 29
Cozy cabin in charming Londonderry
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

10. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is ￥16,471
￥56,580 total
includes taxes & fees
Oct 27 - Oct 28
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

11. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is ￥25,099
￥64,878 total
includes taxes & fees
Nov 3 - Nov 4
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A wooden interior with a kitchen, bar area, and dining space.

12. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (7 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is ￥18,919
￥40,164 total
includes taxes & fees
Nov 2 - Nov 3
The Studio with a View. Bring your dog, too!
A calm lake with a wooden boat on the shore.

13. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is ￥14,118
￥46,088 total
includes taxes & fees
Nov 1 - Nov 2
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

14. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (14 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is ￥24,315
￥71,969 total
includes taxes & fees
Nov 9 - Nov 10
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

15. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is ￥17,993
￥69,434 total
includes taxes & fees
Oct 27 - Oct 28
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

16. Stratton ski-in/ski-out condo steps from the lift with valley-view balcony

Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is ￥11,695
￥49,212 total
includes taxes & fees
Oct 27 - Oct 28
Stratton ski-in/ski-out condo steps from the lift with valley-view balcony
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

17. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Great property and location. Communications with host excellent. Love the privacy and availability of firewood."
United States
Rod M.
The price is ￥16,628
￥66,473 total
includes taxes & fees
Nov 4 - Nov 5
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

18. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (13 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is ￥13,271
￥22,909 total
includes taxes & fees
Oct 27 - Oct 28
Yurt Oasis in the woods of Hinsdale, NH
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

19. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
The price is ￥11,695
￥40,172 total
includes taxes & fees
Nov 2 - Nov 3
Long Trail House 368 condo in Stratton Village, walk to the lifts
A building with a sign reading 'Fire Tower Restaurant & Tavern.'

20. Fourth-floor Stratton Village studio with valley-view balcony

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
The price is ￥11,695
￥35,208 total
includes taxes & fees
Oct 29 - Oct 30
Fourth-floor Stratton Village studio with valley-view balcony
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Brookline Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Great location and wonderful staff! I love staying here every year!"
Kristen 1-night trip
Posted 9 hours ago
The Putney Inn

Find out more about Brookline

Search for holiday rentals in Brookline on Expedia! You can easily find your home rentals, villas, holiday apartments in Brookline using one of the methods below:

  • View our selection of featured holiday rentals in Brookline
  • Use the map to find apartments and other holiday homes in the Brookline neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Brookline while they last

Look no further and take a look at our great range of rental properties in Brookline!

Frequently asked questions

Can I find vacation rentals in Brookline?

Yes, there are vacation rentals near top sights in Brookline, or you can choose a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Brookline?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This vacation home rental outside of Brookline is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Brookline?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Brookline stay.

What’s there to see and do in Brookline?

Explore the area and family-friendly sights such as Brattleboro Bowl, or get out into nature at a spot like West River. In the larger area, you’ll find The Putney School and Townshend State Park.

What’s a vacation rental in Brookline like?

Vacation rentals are private properties where you can stay for a long or short time in Brookline. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.