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Brookline Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Brookline holiday rentals

Property grounds

1. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,370
HK$2,510 total
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
Exterior

2. 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, (170 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 HK$1,334
HK$2,908 total
includes taxes & fees
19 Aug - 20 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Terrace/patio

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, (17 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is HK$706
HK$1,235 total
includes taxes & fees
25 Aug - 26 Aug
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Exterior

4. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$551
HK$2,864 total
includes taxes & fees
13 Aug - 14 Aug
Chalet Mount Snow/Stratton Skiing/hiking
Outdoor pool, a heated pool

5. 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$534
HK$2,492 total
includes taxes & fees
1 Sept - 2 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Private kitchen

6. 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 HK$981
HK$2,056 total
includes taxes & fees
7 Sept - 8 Sept
The Studio with a View. Bring your dog, too!
Terrace/patio

7. 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 HK$1,609
HK$3,697 total
includes taxes & fees
1 Sept - 2 Sept
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Beach

8. 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 HK$636
HK$2,243 total
includes taxes & fees
20 Aug - 21 Aug
Cozy 3 bedroom condo 2.5 miles to Mount Snow
TV, books

9. 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 HK$2,185
HK$2,600 total
includes taxes & fees
13 Aug - 14 Aug
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, fireplace

10. 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 HK$585
HK$2,488 total
includes taxes & fees
10 Sept - 11 Sept
Lovely ski-in/out condo steps from ski lift with trails and amazing views
3 bedrooms

11. 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 HK$2,185
HK$2,711 total
includes taxes & fees
13 Aug - 14 Aug
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Interior

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, (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 HK$1,530
HK$4,008 total
includes taxes & fees
1 Sept - 2 Sept
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior

13. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is HK$585
HK$1,779 total
includes taxes & fees
10 Sept - 11 Sept
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Terrace/patio

14. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$3,139
HK$5,840 total
includes taxes & fees
3 Sept - 4 Sept
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Outdoor spa tub

15. 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 HK$2,464
HK$3,063 total
includes taxes & fees
16 Aug - 17 Aug
Long Trail House at Stratton Mountain Resort
Coffee/tea maker, fridge, microwave, oven

16. 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 HK$1,899
HK$4,531 total
includes taxes & fees
17 Aug - 18 Aug
The MountainTop | Stratton & Mt Snow | Fire Pit
Smart TV, fireplace, Netflix, streaming services

17. 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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is HK$1,347
HK$3,996 total
includes taxes & fees
1 Sept - 2 Sept
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Coffee/tea maker, fridge, microwave, oven

18. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (32 reviews)
"Great space, great location!"
United States
Jason S.
The price is HK$1,236
HK$3,099 total
includes taxes & fees
13 Aug - 14 Aug
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Property grounds

19. 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 HK$2,916
HK$3,615 total
includes taxes & fees
13 Aug - 14 Aug
Large Farmhouse with expansive views, firepit 15 min north of Keene
Lobby

20. 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 HK$824
HK$2,839 total
includes taxes & fees
10 Sept - 11 Sept
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Lovely Hampton. Great staff. Would recommend."
David 1-night trip
Posted 9 hours ago
Hampton Inn Brattleboro

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 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?

Family Friendly Hilltop House In Putney Vermont: This holiday home rental outside of Brookline is located on a lake, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.