Bennington Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Bennington vacation rentals

Interior
Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!

Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!

Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!
2.0 star property
Bennington
10.0 out of 10, Exceptional, (4 reviews)
"This place is a real gem. The location is excellent an having the lake right at your doorstep is fabulous. The house was well equipped and beautifully furnished and had the most comfortable beds we have ever encountered. The fireplace is a real bonus. Overall we property felt very private yet it’s less than five minutes away from town. We hope to stay there again. "
United States
Alan M.
The price is ￥22,736
￥51,050 total
includes taxes & fees
Jan 19 - Jan 20
Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!
Exterior
Quiet Cabin rental near Pat's Peak - Seacoast

Quiet Cabin rental near Pat's Peak - Seacoast

Quiet Cabin rental near Pat's Peak - Seacoast
2.0 star property
Henniker
The price is ￥22,026
￥34,177 total
includes taxes & fees
Jan 13 - Jan 14
Quiet Cabin rental near Pat's Peak - Seacoast
Smart TV, fireplace, printers
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (22 reviews)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is ￥27,710
￥58,161 total
includes taxes & fees
Jan 13 - Jan 14
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School

Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School

Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
2.0 star property
Wilton
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and thoughtful hosts that went above and beyond to make us feel at home. We appreciated the coziness of the house and your kindness. "
United States
Kadie H.
The price is ￥28,420
￥58,932 total
includes taxes & fees
Jan 13 - Jan 14
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
Property grounds
Cottage beside a waterfall

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (11 reviews)
"Very nice property"
United States
Nick
The price is ￥25,262
￥45,398 total
includes taxes & fees
Jan 13 - Jan 14
Cottage beside a waterfall
Exterior detail
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (31 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is ￥13,421
￥26,554 total
includes taxes & fees
Feb 9 - Feb 10
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Property grounds
River Room overlooking the waterfall

River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (3 reviews)
"Had a great time, the grounds are spectacular with the river waterfall in the background. The Bathroom was stunning. Had everything we needed. The bed was super comfy too. The screened-in porch was convenient, too."
United States
Romie G.
The price is ￥25,262
￥45,398 total
includes taxes & fees
Jan 13 - Jan 14
River Room overlooking the waterfall
Interior
Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.4 out of 10, Exceptional, (8 reviews)
"Overall a nice stay!"
United States
Jaymes R.
The price is ￥19,973
￥31,294 total
includes taxes & fees
Jan 13 - Jan 14
Cozy Cabin in a Rural setting-14
Beach
Book your ski vacations for the upcoming season.

Book your ski vacations for the upcoming season.

Book your ski vacations for the upcoming season.
Sutton
10.0 out of 10, Exceptional, (12 reviews)
"House is very clean and comfortable. Kitchen well appointed, Nice location with view of Blaisdell Lake. Several state parks and Lake Sunapee nearby"
United States
Nancy B.
The price is ￥24,868
￥60,216 total
includes taxes & fees
Jan 19 - Jan 20
Book your ski vacations for the upcoming season.
Smart TV
Cozy Cabin in a Rural Setting #16 near Temple,NH

Cozy Cabin in a Rural Setting #16 near Temple,NH

Cozy Cabin in a Rural Setting #16 near Temple,NH
Temple
9.4 out of 10, Exceptional, (17 reviews)
"Bathroom shower could have been cleaner as well as the tile backsplash in kitchen Little noisy because of traffic but can’t do anything about that. Really lovely cabin and area"
United States
Ann M.
The price is ￥21,789
￥35,805 total
includes taxes & fees
Jan 13 - Jan 14
Cozy Cabin in a Rural Setting #16 near Temple,NH
Exterior
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (1 review)
"Place was clean, cozy & very relaxing.. accommodating & communicative host provided us with necessary info for great week! Beautiful lake & landscape was great viewing during surprise snowstorm! Our Thanksgiving week was wonderful as we enjoyed lovely, quiet area in spacious 4 bdrm/2 bath home! Will definitely consider returning"
United States
Jeannie M.
The price is ￥48,456
￥92,490 total
includes taxes & fees
Jan 13 - Jan 14
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Terrace/patio
Private Hot Tub Suite

Private Hot Tub Suite

Private Hot Tub Suite
Antrim
9.0 out of 10, Wonderful, (10 reviews)
"Stayed 3 nights while visiting relatives. Teen loved the Xbox. Had everything we could possibly need. Would definitely stay again."
United States
Dena S.
The price is ￥21,173
￥40,447 total
includes taxes & fees
Jan 14 - Jan 15
Private Hot Tub Suite
Terrace/patio
16 ppl 2 hot tubs, game room, fire pit

16 ppl 2 hot tubs, game room, fire pit

16 ppl 2 hot tubs, game room, fire pit
Antrim
9.8 out of 10, Exceptional, (9 reviews)
"This was a great property. We had a wonderful stay here for a large group. Rebecca is a great host- so responsive and helpful before and during our stay. Highly recommend! "
United States
Kyra D.
The price is ￥28,278
￥63,573 total
includes taxes & fees
Jan 20 - Jan 21
16 ppl 2 hot tubs, game room, fire pit
Interior
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Greenfield
9.8 out of 10, Exceptional, (10 reviews)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is ￥29,210
￥41,972 total
includes taxes & fees
Jan 15 - Jan 16
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Property grounds
Unique Cozy private 1-bedroom apartment in charming Temple

Unique Cozy private 1-bedroom apartment in charming Temple

Unique Cozy private 1-bedroom apartment in charming Temple
Temple
9.8 out of 10, Exceptional, (7 reviews)
"very clean, well decorated, comfortable and peaceful"
United States
Dan G.
The price is ￥55,262
￥68,525 total
includes taxes & fees
Jan 18 - Jan 19
Unique Cozy private 1-bedroom apartment in charming Temple
Fridge, microwave, oven, stovetop
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (2 reviews)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is ￥33,315
￥96,108 total
includes taxes & fees
Jan 13 - Jan 14
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Smart TV, fireplace, video games, table tennis
Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"The hot tub was great and the peace and quiet was very nice."
United States
Brian B.
The price is ￥21,173
￥40,447 total
includes taxes & fees
Jan 15 - Jan 16
Relaxing Hot Tub Getaway
Exterior
Room 08 - King Room - Handicap accessible

Room 08 - King Room - Handicap accessible

Room 08 - King Room - Handicap accessible
Francestown
10.0 out of 10, Exceptional, (1 review)
"This Inn is on my top five hidden gems in my favorite part of NH, the south west.LOCATION: Absolutely stunning property with beautiful vistas looking out across the mountains near and far... AND the largest inground pool with an unobstructed view of the mountains this side of the Mississippi. It's Shangri-La 30 minutes from Manchester. PEOPLE: A husband and wife duo Carrie & Bob operate this historic inn and they really couldn't be more welcoming. They have been embraced by the people of...
United States
Ian T.
The price is ￥29,960
￥36,618 total
includes taxes & fees
Jan 13 - Jan 14
Room 08 - King Room - Handicap accessible
1 bedroom, desk, iron/ironing board, WiFi
Cozy Cabin in a rural setting (#10) In Temple, NH

Cozy Cabin in a rural setting (#10) In Temple, NH

Cozy Cabin in a rural setting (#10) In Temple, NH
Temple
9.0 out of 10, Wonderful, (19 reviews)
"Nice little cabin, clean other cabins are a little close other than that everything was fine "
United States
Lisa G.
The price is ￥18,702
￥32,456 total
includes taxes & fees
Jan 15 - Jan 16
Cozy Cabin in a rural setting (#10) In Temple, NH
Terrace/patio
John's Mountain Hideaway

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
The price is ￥41,051
￥67,668 total
includes taxes & fees
Jan 25 - Jan 26
John's Mountain Hideaway
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

The Carriage Barn Inn

The Carriage Barn Inn

10/10 Excellent
"Very helpful and welcoming host. "
Bruce 1-night trip
Posted 3 days ago
The Carriage Barn Inn

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

  • View our selection of featured holiday rentals in Bennington
  • Use the map to find apartments and other holiday homes in the Bennington neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bennington while they last

Look no further and take a look at our great range of rental properties in Bennington!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Bennington?

Yes, we give you a choice of vacation rentals near popular points of interest in Bennington, or you can choose a secluded option if you're looking for a relaxing stay. Bennington is known for its ski areas.

What are some of the best vacation home rentals that Bennington has to offer?

Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!: This highly rated vacation home rental in Bennington is located on the waterfront and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings.

What’s there to see and do in Bennington?

While exploring the area, visit family-friendly sights like Hardings of Hancock, or get outside and enjoy nature at Contoocook River. In the larger area, you’ll find Crotched Mountain Ski and Ride Area and Crotched Mountain Golf Club.

What’s a vacation rental in Bennington like?

Vacation rentals are privately owned properties you can book for short or long periods in Bennington. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for small groups.