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Brookline Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Brookline vacation rentals

House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin
Coffee/tea maker, fridge, microwave, stovetop

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (20 reviews)
"So cozy, perfect Vermont vacation!"
United States
Evan S.
Hiking Trails On-Site: Cozy Falls Brook Cabin
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (62 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥26,246
￥48,663 total
includes taxes & fees
Aug 10 - Aug 11
Family Friendly Hilltop House In Putney Vermont
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (13 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥14,681
￥66,532 total
includes taxes & fees
Jul 28 - Jul 29
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

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, (169 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 ￥27,851
￥59,084 total
includes taxes & fees
Jul 28 - Jul 29
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
3 bedrooms

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Walpole
10.0 out of 10, Exceptional, (6 reviews)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
The price is ￥43,079
￥53,140 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
The price is ￥45,614
￥56,425 total
includes taxes & fees
Jul 29 - Jul 30
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

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.
The price is ￥43,703
￥93,824 total
includes taxes & fees
Aug 17 - Aug 18
The MountainTop | Stratton & Mt Snow | Fire Pit
Private kitchen

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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
The price is ￥18,873
￥40,956 total
includes taxes & fees
Aug 3 - Aug 4
The Studio with a View. Bring your dog, too!
Terrace/patio

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, (19 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is ￥36,862
￥81,457 total
includes taxes & fees
Aug 4 - Aug 5
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Interior

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, (9 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 ￥30,309
￥81,457 total
includes taxes & fees
Aug 25 - Aug 26
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (5 reviews)
"It was a very pleasant & peaceful night! They were very pleasant, helpful & very detailed when giving all the information/instructions on how to check in & how to use the incinerator toilet! Places to eat ,hike etc…."
United States
Julie
The price is ￥18,283
￥28,726 total
includes taxes & fees
Jul 28 - Jul 29
Yurt Oasis in the woods of Hinsdale, NH
Beach

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)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is ￥14,745
￥48,134 total
includes taxes & fees
Aug 20 - Aug 21
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Outdoor spa tub

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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is ￥50,430
￥62,686 total
includes taxes & fees
Jul 30 - Jul 31
Long Trail House at Stratton Mountain Resort
Property grounds

Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene
Walpole
The price is ￥57,491
￥70,910 total
includes taxes & fees
Jul 28 - Jul 29
Large Farmhouse with expansive views, firepit 15 min north of Keene
Exterior

Chalet-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK

Chalet-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
Jamaica
8.0 out of 10, Very Good, (3 reviews)
"Host was welcoming. Everything was clean and in excellent order."
United States
Christopher C.
The price is ￥22,936
￥41,839 total
includes taxes & fees
Jul 28 - Jul 29
Chalet-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
TV, fireplace

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very Good, (35 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 ￥12,214
￥51,396 total
includes taxes & fees
Jul 28 - Jul 29
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Interior

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.6 out of 10, Exceptional, (24 reviews)
"Super attentive and accommodating host! It was a perfect cozy getaway on a frigid weekend, and the fireplace and hot tub were just the ticket. "
United States
Meghan R.
The price is ￥32,202
￥94,520 total
includes taxes & fees
Jul 28 - Jul 29
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Outdoor pool, a heated pool

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 ￥33,264
￥82,203 total
includes taxes & fees
Jul 31 - Aug 1
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Lobby

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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 ￥17,202
￥59,275 total
includes taxes & fees
Jul 30 - Jul 31
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"The staff were all courteous and professional. The room was clean, housekeeping staff were friendly. The breakfast was amazing with so many choices of food. Lori was a prize of an employee running the breakfast room! Can’t think of any negatives at all."
Kathryn 2-night trip
Posted less than an hour ago
Best Western Plus Keene 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
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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?

Everything you need - swim, relax, play outside!: This vacation home rental outside of Brookline is located in the mountains and has an indoor pool, a fireplace, 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 patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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. In the larger area, you’ll find The Putney School and Landmark College.

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.