Brookline Vacation Rentals

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Check prices for these dates

Tonight
Dec 10 - Dec 11
Tomorrow
Dec 11 - Dec 12
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Brookline vacation rentals

Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is ￥61,815
￥76,835 total
includes taxes & fees
Dec 15 - Dec 16
Long Trail House at Stratton Mountain Resort
3 bedrooms, desk, iron/ironing board, travel crib
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Camping in Dover

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
8.0 out of 10, Very Good, (2)
"Place was amazing! Beautiful property and so unique. Being pet friendly was a huge plus! We had a wonderful time!"
United States
Alexia R.
The price is ￥62,571
￥79,743 total
includes taxes & fees
Dec 14 - Dec 15
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
3 bedrooms, internet, bed sheets
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Vacation Home in Andover

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
9.0 out of 10, Wonderful, (29)
"Really nice house in a beautiful place. We had a great time. Plenty of space with multiple bedrooms and bathrooms are great. Great kitchen and grill made it easy to feed lots of people. Also lots of great things to do in the house already. One criticism for me was the screen doors. They were not all set in the rails and some of them had holes that let bugs in. It got a bit warm in the house during the day time with no air conditioning so it would’ve been better if the screen doors were...
United States
Dan T.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Property grounds
Owl's Nest Treehouse

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is ￥42,829
￥52,385 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Owl's Nest Treehouse
Interior
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Vacation Home in Dover

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
10.0 out of 10, Exceptional, (11)
"Beautiful new home, great for big family and friend groups. Comfortable bedding and furniture. Lots of open space and seating "
United States
Gena L.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Fridge, microwave, oven, stovetop
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Vacation Home in Dover

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
9.8 out of 10, Exceptional, (48)
"Overall a nice stay, thanks Jen!"
United States
Anonymous traveler
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Fridge, microwave, oven, stovetop
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Vacation Home in Dover

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
The price is ￥112,205
￥217,878 total
includes taxes & fees
Dec 12 - Dec 13
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Fridge, microwave, oven, stovetop
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Cabin in Dover

Cozy 2-bedroom cabin near Mount Snow 3 min drive
2.0 star property
9.6 out of 10, Exceptional, (9)
"I really enjoyed every aspect of my stay here and highly recommend the property. "
United States
Gregory G.
Cozy 2-bedroom cabin near Mount Snow 3 min drive
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Vacation Home in Wardsboro

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (29)
"This place is enormous with nooks and crannies everywhere to get away, shoot pool, play video games, read, swim, sit in the sauna,barbecue, or wade in the brook below! Some of the rooms are great for a couple, others are better for a bunch of kids who are willing to sleep in a bunk or twin bed. "
United States
khs
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Outdoor pool, a heated pool
Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Vacation Home in Weston

Charming mountain retreat with pool, fire pit, glamping loft, and endless views
9.8 out of 10, Exceptional, (9)
"An absolutely incredible home and property for a week long end of summer vacation. The setting, atmosphere, decor and attention to detail were all top notch and we couldn’t have been happier. We particularly loved the layout and all of the amenities. This property is a true winner for any season, and we cannot wait to return for a winter retreat! "
United States
Chris L.
Charming mountain retreat with pool, fire pit, glamping loft, and endless views
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Vacation Home in Jamaica

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
9.6 out of 10, Exceptional, (21)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
The price is ￥37,069
￥132,085 total
includes taxes & fees
Dec 16 - Dec 17
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Interior
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Cabin in Londonderry

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
8.6 out of 10, Excellent, (8)
"We had a wonderful stay."
United States
Joshua
The price is ￥51,161
￥88,260 total
includes taxes & fees
Dec 22 - Dec 23
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Property grounds
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Chalet in Wilmington

Beautiful Lodging at Mount Snow with Hot Tub on Deck
9.4 out of 10, Exceptional, (42)
"My family and I loved our stay. This cabin had everything we needed and more. One thing we do wish we had was fans in the upstairs rooms, as we stayed in the summer time and it did get quite hot up there. The owners were very helpful, and amazing with communication. We would absolutely love to stay here again one day! "
United States
lizzie m.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Smart TV, fireplace, DVD player, table tennis
Beautiful Custom Built Timber Frame Home, Sleeps 11

Vacation Home in Wilmington

Beautiful Custom Built Timber Frame Home, Sleeps 11
10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Exterior
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is ￥6,944
￥41,162 total
includes taxes & fees
Dec 14 - Dec 15
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Fridge, microwave, stovetop, dishwasher
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Apartment in Dover

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
9.6 out of 10, Exceptional, (5)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
The price is ￥34,500
￥79,920 total
includes taxes & fees
Dec 15 - Dec 16
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Terrace/patio
LUX property, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV

Vacation Home in Townshend

LUX property, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV
10.0 out of 10, Exceptional, (7)
LUX property, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV
Terrace/patio
Stratton South Long Trail Studio Adjacent to the Village and Lifts

Apartment in Stratton

Stratton South Long Trail Studio Adjacent to the Village and Lifts
9.4 out of 10, Exceptional, (68)
"This studio apartment is cozy and comfortable, with a balcony offering great views. The kitchen is clean and functional, and indoor parking is very convenient."
United States
GO PIN
Stratton South Long Trail Studio Adjacent to the Village and Lifts
Fridge, microwave, oven, stovetop
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces

Vacation Home in West Dover

Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces
8.2 out of 10, Very Good, (10)
"Lovely place for a large group of people."
United States
Nicole M.
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces
1 bedroom, WiFi, bed sheets
Romantic Riverbed Treehouse - hot tub & new sauna!

Cabin in londonderry

Romantic Riverbed Treehouse - hot tub & new sauna!
10.0 out of 10, Exceptional, (2)
"We had a great stay. The cabin was well lit and perfect for two people. Very clean, warm, and comfortable. There was a snow storm the night before we left and they kept the driveway plowed for us. Gorgeous views and close to everything."
United States
Karen L.
The price is ￥29,295
￥99,802 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Romantic Riverbed Treehouse - hot tub & new sauna!
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Our room was very clean. Comfy bed. Loved the uniqueness of this hotel! Will come again!"
LuAnn 1-night trip
Posted 3 days ago
Latchis Hotel

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!

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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?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This vacation home rental outside of Brookline is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Brookline?

With 4 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. Other popular places to visit in the area include Stratton Mountain Resort and Mount Snow.

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.