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Brookline Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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.
$232 nightly
The price is $259
Nov 5 - Nov 6
Total with taxes and fees
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.
$243 nightly
The price is $272
Nov 9 - Nov 10
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A wooden house with a porch lit by string lights, surrounded by snow.

3. 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.
$342 nightly
The price is $387
Nov 5 - Nov 6
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
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
10.0 out of 10, Exceptional, (2 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
$84 nightly
The price is $95
Nov 30 - Dec 1
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
A red house with a covered porch and a chimney.

5. 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, (175 reviews)
"We had such a great time! Those is a well taken care of, clean, cozy property. We would absolutely visit again!!"
United States
Kathy H.
$332 nightly
The price is $372
Nov 5 - Nov 6
Total with taxes and fees
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.

6. 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.
$112 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

7. 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, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$138 nightly
The price is $150
Nov 30 - Dec 1
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

8. 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.
$232 nightly
The price is $262
Nov 5 - Nov 6
Total with taxes and fees
Cozy cabin in charming Londonderry
A covered porch with a dark wooden exterior, a wooden deck, and a black door.

9. 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.
$355 nightly
The price is $401
Nov 9 - Nov 10
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A room with a wood-burning stove, a brick fireplace, a mounted television, and a sign above the fireplace.

10. 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.
$248 nightly
The price is $280
Nov 11 - Nov 12
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A spacious cabin with a wooden interior, a dining area, a sofa, and a fireplace.

11. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
$559 nightly
The price is $632
Nov 11 - Nov 12
Total with taxes and fees
Cozy Cedar Cabin 8 Min to Mount Snow
A hallway with a bench, a wall-mounted towel rack, and a door leading to an outdoor area.

12. 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.
$415 nightly
The price is $469
Nov 9 - Nov 10
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A swimming pool with a stone border, surrounded by a snow-covered landscape and a wooden fence.

13. Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (85 reviews)
"Clean well, equipped room. Great amenities, wonderful proximity to all the action in the village,easy parking and access throughout the facility."
United States
Michael
$391 nightly
The price is $441
Nov 5 - Nov 6
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
A wooden interior with a kitchen, bar area, and dining space.

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

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (8 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.
$225 nightly
The price is $252
Nov 18 - Nov 19
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

15. 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
$232 nightly
The price is $262
Nov 5 - Nov 6
Total with taxes and fees
Long Trail House 368 condo in Stratton Village, walk to the lifts
A wooden interior with a staircase, dining area, and kitchen.

16. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
Wardsboro
9.6 out of 10, Exceptional, (4 reviews)
"Everything was wonderful and perfect for our family. Super clean and great Vermont experience"
United States
Lisa B.
$414 nightly
The price is $467
Nov 5 - Nov 6
Total with taxes and fees
The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

17. 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.
$277 nightly
The price is $314
Nov 9 - Nov 10
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A wooden deck with a table set for a meal, featuring a plate of food, glasses of wine, and a bowl of dip.

18. The MountainTop | Stratton & Mt Snow | Fire Pit

The MountainTop | Stratton & Mt Snow | Fire Pit
Stratton
10.0 out of 10, Exceptional, (10 reviews)
"Lovely place to stay. The stars truly are stunning. "
United States
Brenna G.
$431 nightly
The price is $487
Nov 5 - Nov 6
Total with taxes and fees
The MountainTop | Stratton & Mt Snow | Fire Pit
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

19. 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.
$325 nightly
The price is $367
Nov 5 - Nov 6
Total with taxes and fees
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
A building with a sign reading 'Landmark' and a large spherical sculpture in the center.

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

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
$205 nightly
The price is $232
Nov 5 - Nov 6
Total with taxes and fees
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
"Quiet, clean, safe area. Good breakfast- fruit, yogurt, waffles plus all the usual cereal, toast etc."
Martha 1-night trip
Posted 4 hours ago
The Putney Inn

Find out more about Brookline

Everything you need to know about Brookline vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Brookline vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brookline vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Brookline vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brookline. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Brookline in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $252 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Brookline rentals

At Expedia, we put the best Brookline vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Brookline rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brookline vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brookline. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.