Brookline Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Brookline holiday rentals

Terrace/patio

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, (12 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is HK$705
HK$1,232 total
includes taxes & fees
15 May - 16 May
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
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)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is HK$1,331
HK$2,797 total
includes taxes & fees
18 May - 19 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$1,558
HK$1,913 total
includes taxes & fees
19 May - 20 May
Vikings Villages Resort - Double Bed Room
Exterior

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 HK$1,253
HK$2,245 total
includes taxes & fees
28 May - 29 May
Wellness Getaway with a Personal Sauna, and Private River Beach!
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 HK$533
HK$2,548 total
includes taxes & fees
17 May - 18 May
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is HK$2,153
HK$2,659 total
includes taxes & fees
17 May - 18 May
Owl's Nest Treehouse
Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
7.8 out of 10, Good, (58 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
The price is HK$556
HK$1,899 total
includes taxes & fees
17 May - 18 May
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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, (2 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 HK$987
HK$2,043 total
includes taxes & fees
20 May - 21 May
The Studio with a View. Bring your dog, too!
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (23 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is HK$1,397
HK$2,697 total
includes taxes & fees
20 May - 21 May
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is HK$431
HK$637 total
includes taxes & fees
15 May - 16 May
2 private mountain RV pads for rent. Full hook ups
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,374
HK$2,503 total
includes taxes & fees
27 May - 28 May
Family Friendly Hilltop House In Putney Vermont
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
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$2,018
HK$2,402 total
includes taxes & fees
17 May - 18 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds

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, (34 reviews)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is HK$556
HK$2,413 total
includes taxes & fees
16 May - 17 May
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is HK$665
HK$1,592 total
includes taxes & fees
31 May - 1 Jun
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"Poor management company. Great lodge. "
United States
Billy W.
The price is HK$1,041
HK$3,042 total
includes taxes & fees
15 May - 16 May
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is HK$1,198
HK$4,083 total
includes taxes & fees
21 May - 22 May
Outdoor Adventure Hub! Family Home in West Dover
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$917
HK$3,449 total
includes taxes & fees
20 May - 21 May
Chalet Mount Snow/Stratton Skiing/hiking
4 bedrooms, travel cot, Internet, bed sheets

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"The house was just as listed. Everything we needed was there for us upon arrival. The host is amazing and was happy to welcome us in their home. We would definitely come back"
United States
Louis
The price is HK$1,073
HK$4,239 total
includes taxes & fees
16 May - 17 May
Outdoor Adventure Hub! Family Home in West Dover
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, (51 reviews)
"Cozy place, very close to the moover and Mount Snow. Host was very responsive. Would definitely book again!"
United States
dory p.
The price is HK$705
HK$2,282 total
includes taxes & fees
20 May - 21 May
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

6/10 Okay
"Room was clean. "
Kathleen 1-night trip
Posted 6 hours ago
Comfort Inn & Suites Brattleboro I-91

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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  • 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 holiday rentals in Brookline?

Yes, there are holiday rentals close to the most popular sights in Brookline, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Brookline has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: This holiday home rental outside of Brookline is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Brookline?

With 5 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find The Putney School and Townshend State Park.

What’s a holiday rental in Brookline like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brookline. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for small groups.