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Holiday Rentals in Brattleboro

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Holiday Rentals in Brattleboro

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (56)
"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."
The Jelly Mill-A Peaceful River Retreat

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is €353
includes taxes & fees
19 Aug - 20 Aug
Long Trail House at Stratton Mountain Resort

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (53)
"Great place just need the fire place to be fixed asap, especially for the winter time"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

9.4 out of 10, Exceptional, (26)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is €178
includes taxes & fees
4 Aug - 5 Aug
Lovely 2nd Floor Apartment

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

10.0 out of 10, Exceptional, (5)
"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Bear Creek Cabin

10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
The price is €532
includes taxes & fees
11 Aug - 12 Aug
Bear Creek Cabin

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is €604
includes taxes & fees
1 Sept - 2 Sept
The Mountain Escape!

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.2 out of 10, Wonderful, (40)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (103)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (129)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

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

9.4 out of 10, Exceptional, (16)
"Highly recommend clean beautiful stay!"
The price is €230
includes taxes & fees
5 Aug - 6 Aug
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck

8.6 out of 10, Excellent, (11)
"When we first arrived we couldn’t find extra trash bags. We sent a message to the host, Jason, and he replied immediately to assist us. I appreciate the attentiveness and genuine hospitality. This place is cozy and clean. Made for the perfect weekend getaway!"
Stratton Ski Chalet: Spacious Modern Oasis w/Hot Tub, Fireplace, Pond & BBQ Deck

Riverside Retreat – Cozy 2-Story Getaway!

9.8 out of 10, Exceptional, (27)
"Interior amazing. Exterior could use some attention"
Riverside Retreat – Cozy 2-Story Getaway!

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (49)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (44)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

10.0 out of 10, Exceptional, (1)
"This was the definition of a New England inn!! Super cute and the staff were fantastic! They were so helpful! I would definitely stay here again!! "
The price is €182
includes taxes & fees
4 Aug - 5 Aug
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very good, (29)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (158)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is €323
includes taxes & fees
19 Aug - 20 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (15)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is €423
includes taxes & fees
6 Aug - 7 Aug
Downtown Hot Tub Escape
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 Brattleboro Hotel Reviews

Frequently asked questions

Are there holiday rentals in Brattleboro?

Yes, there are holiday rentals in Brattleboro close to Brattleboro Bowl, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and ski slopes in Brattleboro. Leave some time to check out the shops and entertainment venues during your trip.

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

The Jelly Mill-A Peaceful River Retreat: This highly rated holiday home rental in Brattleboro is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Brattleboro?

Expedia has 19 holiday rentals for your stay in Brattleboro.

What can I see and do in Brattleboro?

Enjoy the outdoors at Brattleboro Common and Hogback Mountain Conservation Area, or simply take in cultural attractions like The Stone Church and Tasha Tudor Museum. Other places in town to visit include Latchis Theatre and Vermont Marketplace.

What’s a holiday rental in Brattleboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brattleboro. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.