We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Brattleboro Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Bedrooms
Any
Bathrooms
Any
Suitability
Show more
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
49 rentals in Brattleboro.
Sort by:
Tripadvisor Sort
Serenity Cottage in Southern Vermont…, holiday rental in Brattleboro

Serenity Cottage in Southern Vermont…

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Large modern house with huge open great room and four large bedrooms with baths, holiday rental in Brattleboro

Large modern house with huge open great room and four large bedrooms with baths

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mt. Snow Paradise - Indoor Jacuzzi & Sauna - Minutes to Mountain - Sleeps 10, holiday rental in Brattleboro

Mt. Snow Paradise - Indoor Jacuzzi & Sauna - Minutes to Mountain - Sleeps 10

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont!  Come Explore!, holiday rental in Brattleboro

Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont! Come Explore!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Vacation Log Home In Southern Vermont, holiday rental in Brattleboro

Vacation Log Home In Southern Vermont

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Perfect - Cozy  Townhouse in Mount Snow- Vt, holiday rental in Brattleboro

Perfect - Cozy Townhouse in Mount Snow- Vt

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spectacular 4 Season Home On Spruce Lake Near Mt. Snow, holiday rental in Brattleboro

Spectacular 4 Season Home On Spruce Lake Near Mt. Snow

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mount Snow opening November 25! Reserve your stay now!, holiday rental in Brattleboro

Mount Snow opening November 25! Reserve your stay now!

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, holiday rental in Brattleboro

Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Winter Ski & Snowmobile;  6 bedrooms + Garage, holiday rental in Brattleboro

Winter Ski & Snowmobile; 6 bedrooms + Garage

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Brattleboro rentals sent straight to your email!
Beautiful House overlooking Spofford Lake, holiday rental in Brattleboro

Beautiful House overlooking Spofford Lake

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Magical Lakefront Home on Forest Lake, holiday rental in Brattleboro

Magical Lakefront Home on Forest Lake

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Pet And Family Friendly Hilltop House In Putney Vermont, holiday rental in Brattleboro

Pet And Family Friendly Hilltop House In Putney Vermont

0 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Manor-Stunning Modern Farmhouse with Swim Pond, holiday rental in Brattleboro

The Manor-Stunning Modern Farmhouse with Swim Pond

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Brattleboro

Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford

4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Waterfront Lake Raponda Vacation Paradise, holiday rental in Brattleboro

Waterfront Lake Raponda Vacation Paradise

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spring Escape, Get away in the falls❤️, holiday rental in Brattleboro

Spring Escape, Get away in the falls❤️

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Quiet Vermont Home Close To Everything, holiday rental in Brattleboro

Quiet Vermont Home Close To Everything

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Vermont Log Cabin w/ Amazing Views, Close to Mount Snow, holiday rental in Brattleboro

Vermont Log Cabin w/ Amazing Views, Close to Mount Snow

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Vermont Log Cabin available for weekend and weekly, holiday rental in Brattleboro

Vermont Log Cabin available for weekend and weekly

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
BaseCamp Mogul Retreat, holiday rental in Brattleboro

BaseCamp Mogul Retreat

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mountain View Retreat - Close to all year round activities, holiday rental in Brattleboro

Mountain View Retreat - Close to all year round activities

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Mt. Snow/Lake Raponda, holiday rental in Brattleboro

Mt. Snow/Lake Raponda

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Main House - Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Brattleboro

Main House - Relax and enjoy the scenery, go and swim, fish or start your boat

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Secluded dog-friendly home w/ wood burning fireplace, Internet, & forest views!, holiday rental in Brattleboro

Secluded dog-friendly home w/ wood burning fireplace, Internet, & forest views!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Bright three-level home w/water views, jetted tub, firepit, and more!, holiday rental in Brattleboro

Bright three-level home w/water views, jetted tub, firepit, and more!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful Lake Side Getaway, Quiet, and Peaceful, holiday rental in Brattleboro

Beautiful Lake Side Getaway, Quiet, and Peaceful

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Affordable Spacious Vacation Home on Lake Spofford, holiday rental in Brattleboro

Affordable Spacious Vacation Home on Lake Spofford

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Hilltop Home with Great Views, holiday rental in Brattleboro

Hilltop Home with Great Views

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Penthouse - Steps to the Sandy Beach & clear water, holiday rental in Brattleboro

Penthouse - Steps to the Sandy Beach & clear water

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Lake house getaway on pristine Spofford Lake, New Hampshire, holiday rental in Brattleboro

Lake house getaway on pristine Spofford Lake, New Hampshire

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Stay at a Craft Brewery, holiday rental in Brattleboro

Stay at a Craft Brewery

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A Healing Forest Space in the Heart of New England, holiday rental in Brattleboro

A Healing Forest Space in the Heart of New England

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more, holiday rental in Brattleboro

Charming, rural house w/shared tennis, private Ping-Pong table, Foosball, & more

4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PARADISE on EARTH! - Historic 4BR Farmhouse, holiday rental in Brattleboro

PARADISE on EARTH! - Historic 4BR Farmhouse

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Stunning Forest Lake Home with Hot Tub open all Yr, holiday rental in Brattleboro

Stunning Forest Lake Home with Hot Tub open all Yr

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Steps to the sandy beach, holiday rental in Brattleboro

Steps to the sandy beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Welcoming, warm, cozy but expansive 1800s Farmhouse with 21st century amenities!, holiday rental in Brattleboro

Welcoming, warm, cozy but expansive 1800s Farmhouse with 21st century amenities!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Marlboro, Vermont Ski House - discount offered, holiday rental in Brattleboro

Marlboro, Vermont Ski House - discount offered

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
BaseCamp Mogul: Green Mountain Retreat, holiday rental in Brattleboro

BaseCamp Mogul: Green Mountain Retreat

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped, holiday rental in Brattleboro

Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Brattleboro

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Church sanctuary, holiday rental in Brattleboro

Church sanctuary

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casual lux near Hermitage Club & Four Columns Inn, holiday rental in Brattleboro

Casual lux near Hermitage Club & Four Columns Inn

4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tentrr Signature Site - Hillside Camp, holiday rental in Brattleboro

Tentrr Signature Site - Hillside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Crafts Inn in Vermont 1BR Suite, SATURDAY Check-In, holiday rental in Brattleboro

Crafts Inn in Vermont 1BR Suite, SATURDAY Check-In

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PoshHaus Court ST Colonial, holiday rental in Brattleboro

PoshHaus Court ST Colonial

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Jabulani Luxury Rural Stay, holiday rental in Brattleboro

Jabulani Luxury Rural Stay

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10, holiday rental in Brattleboro

Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Brattleboro