Brookline Vacation Rentals

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Dates

November 2026

December 2026

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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

Putney

Susan G.

AED 986 total

includes taxes & fees

9 Nov - 10 Nov

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!

Newfane

Joseph P.

AED 1,020 total

includes taxes & fees

16 Nov - 17 Nov

A wooden house with a porch lit by string lights, surrounded by snow.

3. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Chelsea G.

AED 1,438 total

includes taxes & fees

8 Nov - 9 Nov

A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

4. Cozy Vermont Tiny Home Get Away

Brattleboro

Anthony L.

AED 349 total

includes taxes & fees

30 Nov - 1 Dec

A red house with a covered porch and a chimney.

5. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Kathy H.

AED 1,366 total

includes taxes & fees

9 Nov - 10 Nov

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

Dover

Ava M.

AED 465 total

includes taxes & fees

9 Nov - 10 Nov

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

Hinsdale

Adrienne

AED 600 total

includes taxes & fees

9 Nov - 10 Nov

A view through a window with a wooden frame, revealing a forested area with snow on the ground.

8. Cozy cabin in charming Londonderry

Londonderry

Eric H.

AED 961 total

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

9. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Wardsboro

Jeff H.

AED 1,544 total

includes taxes & fees

9 Nov - 10 Nov

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

West Dover

Scott S.

AED 1,029 total

includes taxes & fees

11 Nov - 12 Nov

A spacious cabin with a wooden interior, a dining area, a sofa, and a fireplace.

11. Cozy Cedar Cabin 8 Min to Mount Snow

Dover

AED 2,299 total

includes taxes & fees

11 Nov - 12 Nov

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!

Wardsboro

Carly L.

AED 1,702 total

includes taxes & fees

9 Nov - 10 Nov

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

Stratton

Michael

AED 1,621 total

includes taxes & fees

8 Nov - 9 Nov

A wooden interior with a kitchen, bar area, and dining space.

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

Brattleboro

James M.

AED 877 total

includes taxes & fees

18 Nov - 19 Nov

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

Stratton

AED 963 total

includes taxes & fees

8 Nov - 9 Nov

A wooden interior with a staircase, dining area, and kitchen.

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

Wardsboro

Lisa B.

AED 1,717 total

includes taxes & fees

9 Nov - 10 Nov

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

Dover

Tania J.

AED 1,152 total

includes taxes & fees

9 Nov - 10 Nov

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

Stratton

Brenna G.

AED 1,789 total

includes taxes & fees

6 Nov - 7 Nov

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

Dover

Evan C.

AED 1,349 total

includes taxes & fees

6 Nov - 7 Nov

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

Stratton

AED 851 total

includes taxes & fees

6 Nov - 7 Nov

View all properties

Find vacation rentals that suit your style

Top Brookline Hotel Reviews

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A modern outdoor lounge area with two lounge chairs and a wooden deck.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A dock extending into a lake with a grassy area in the foreground and trees in the background.

Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

10/10 Excellent

James

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

A stone fire pit with flames in front of a house with a covered porch and blue lighting.

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

10/10 Excellent

Anthony

A large, two-story house with a snow-covered driveway and surrounding trees.

Chesterfield Inn

West Chesterfield

10/10 Excellent

Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.

Beverly

A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

Inn on Putney Road

Brattleboro

10/10 Excellent

Victoria

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

Comfort Inn & Suites Brattleboro I-91

Brattleboro

10/10 Excellent

Julianne

A modern living room with a fireplace, large windows, and a cozy seating area.

Inn At Mount Snow

West Dover

10/10 Excellent

Peter

A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

Hampton Inn Brattleboro

Brattleboro

10/10 Excellent

Arrived late and were greeted by 2 friendly associates at the desk. There were coffee, tea, hot cocoa, cookies, cheese and crackers available. A welcoming lobby with fireplace. Room was nice, comfortable and clean. Lots of outlets in room. Indoor pool was nice, clean, and heated. hot tub was very relaxing after days of skiing. Continental breakfast was very good and had a variety of choices. We were pleasantly surprised with our choice.

K.White

Latchis Hotel

Brattleboro

10/10 Excellent

Anonymous traveler

A two-story house with a stone staircase leading to a wooden front door.

The Inn At Quail Run

Wilmington

10/10 Excellent

Lydia

A dining table with a bottle of champagne, a glass, and a plate of cheese and fruits.

Farm Road Estate

West Dover

10/10 Excellent

Rosa

An outdoor deck with a wooden table and wicker chairs, surrounded by a wooden railing and string lights.

The Wilmington Inn

Wilmington

10/10 Excellent

Sophia

A large, white colonial-style house with a porch, surrounded by lush greenery and trees.

The White House Inn

Wilmington

10/10 Excellent

Rya

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

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.

Brookline Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Brookline vacation rentals

1. Family Friendly Hilltop House In Putney Vermont

2. Wellness Getaway with a Personal Sauna, and Private River Beach!

3. Chalet Mount Snow/Stratton Skiing/hiking

4. Cozy Vermont Tiny Home Get Away

5. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

6. The Eagles Wing at The CHM - Private Apartment

7. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

8. Cozy cabin in charming Londonderry

9. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

10. Cozy 3 bedroom condo 2.5 miles to Mount Snow

11. Cozy Cedar Cabin 8 Min to Mount Snow

12. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

13. Long Trail House at Stratton Mountain Resort

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

15. Long Trail House 368 condo in Stratton Village, walk to the lifts

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

17. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

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

19. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

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

Find vacation rentals that suit your style

Top Brookline Hotel Reviews

Four Columns Inn

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Brookline?

What's the top vacation rental in Brookline?

How many vacation rentals are there in Brookline?

What’s there to see and do in Brookline?

What’s a vacation rental in Brookline like?