Bennington Holiday Rentals

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Check prices for these dates

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

Our top choices for Bennington holiday rentals

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

Holiday Home in Bennington

Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Stayed for a quick night ahead of skiing at Crotched. Great location near the mountain. Place was super cute, clean and comfortable for our family of four. "
United States
Jessica H.
The price is HK$1,122
HK$2,520 total
includes taxes & fees
21 Jan - 22 Jan
Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!
Exterior
Quiet Cabin rental near Pat's Peak - Seacoast

Cabin in Henniker

Quiet Cabin rental near Pat's Peak - Seacoast
2.0 star property
The price is HK$1,087
HK$1,687 total
includes taxes & fees
26 Jan - 27 Jan
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

Cottage in Rindge

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
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 HK$1,368
HK$2,897 total
includes taxes & fees
22 Jan - 23 Jan
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

Apartment in Wilton

Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
2.0 star property
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 HK$1,403
HK$2,909 total
includes taxes & fees
21 Jan - 22 Jan
Spacious & Historic 2-Bed – 5 Min Drive to High Mowing, 25 Min to Dublin School
Property grounds
Cottage beside a waterfall

Cottage in Wilton

Cottage beside a waterfall
10.0 out of 10, Exceptional, (11 reviews)
"Very nice property"
United States
Nick
The price is HK$1,247
HK$2,241 total
includes taxes & fees
15 Jan - 16 Jan
Cottage beside a waterfall
Exterior detail
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Apartment in Peterborough

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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 HK$663
HK$1,311 total
includes taxes & fees
9 Feb - 10 Feb
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Property grounds
River Room overlooking the waterfall

Apartment in Wilton

River Room overlooking the waterfall
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 HK$1,247
HK$2,241 total
includes taxes & fees
26 Jan - 27 Jan
River Room overlooking the waterfall
Interior
Cozy Cabin in a Rural setting-14

Cabin in Temple

Cozy Cabin in a Rural setting-14
9.4 out of 10, Exceptional, (8 reviews)
"Overall a nice stay!"
United States
Jaymes R.
The price is HK$986
HK$1,570 total
includes taxes & fees
21 Jan - 22 Jan
Cozy Cabin in a Rural setting-14
Beach
Book your ski vacations for the upcoming season.

Holiday Home in Sutton

Book your ski vacations for the upcoming season.
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 HK$1,228
HK$2,973 total
includes taxes & fees
19 Jan - 20 Jan
Book your ski vacations for the upcoming season.
Smart TV
Cozy Cabin in a Rural Setting #16 near Temple,NH

Cabin in Temple

Cozy Cabin in a Rural Setting #16 near Temple,NH
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 HK$1,076
HK$1,793 total
includes taxes & fees
21 Jan - 22 Jan
Cozy Cabin in a Rural Setting #16 near Temple,NH
Exterior
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Holiday Home in Stoddard

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
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 HK$2,534
HK$4,805 total
includes taxes & fees
2 Feb - 3 Feb
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Terrace/patio
Private Hot Tub Suite

Holiday Home in Antrim

Private Hot Tub Suite
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 HK$1,046
HK$1,997 total
includes taxes & fees
14 Jan - 15 Jan
Private Hot Tub Suite
Terrace/patio
16 ppl 2 hot tubs, game room, fire pit

Holiday Home in Antrim

16 ppl 2 hot tubs, game room, fire pit
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 HK$1,396
HK$3,139 total
includes taxes & fees
20 Jan - 21 Jan
16 ppl 2 hot tubs, game room, fire pit
Interior
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Cabin in Greenfield

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
9.8 out of 10, Exceptional, (10 reviews)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is HK$1,442
HK$2,055 total
includes taxes & fees
22 Jan - 23 Jan
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Property grounds
Unique Cozy private 1-bedroom apartment in charming Temple

Apartment in Temple

Unique Cozy private 1-bedroom apartment in charming Temple
9.8 out of 10, Exceptional, (7 reviews)
"Our stay was great. I loved the apartment and wish we had been there longer to enjoy the outdoors as well."
United States
Julia P.
The price is HK$2,728
HK$3,383 total
includes taxes & fees
22 Jan - 23 Jan
Unique Cozy private 1-bedroom apartment in charming Temple
Fridge, microwave, oven, stovetop
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Holiday Home in Keene

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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 HK$1,645
HK$4,711 total
includes taxes & fees
19 Jan - 20 Jan
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Smart TV, fireplace, video games, ping pong
Relaxing Hot Tub Getaway

Holiday Home in Antrim

Relaxing Hot Tub Getaway
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 HK$1,046
HK$1,997 total
includes taxes & fees
15 Jan - 16 Jan
Relaxing Hot Tub Getaway
Exterior
Room 08 - King Room - Handicap accessible

Apartment in Francestown

Room 08 - King Room - Handicap accessible
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 HK$1,479
HK$1,834 total
includes taxes & fees
14 Jan - 15 Jan
Room 08 - King Room - Handicap accessible
1 bedroom, desk, iron/ironing board, WiFi
Cozy Cabin in a rural setting (#10) In Temple, NH

Cabin in Temple

Cozy Cabin in a rural setting (#10) In Temple, NH
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 HK$923
HK$1,611 total
includes taxes & fees
21 Jan - 22 Jan
Cozy Cabin in a rural setting (#10) In Temple, NH
Terrace/patio
John's Mountain Hideaway

Holiday Home in Jaffrey

John's Mountain Hideaway
The price is HK$1,584
HK$2,861 total
includes taxes & fees
2 Feb - 3 Feb
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.
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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 4 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
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Look no further and take a look at our great range of rental properties in Bennington!

Frequently asked questions

Can I find holiday rentals in Bennington?

Yes, there are holiday rentals close to the most popular sights in Bennington, or you can select a more secluded option if you're looking for a relaxing stay. Bennington is known for its ski areas.

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

Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!: This highly rated holiday 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 wider area, you’ll find Crotched Mountain Ski and Ride Area and Crotched Mountain Golf Club.

What’s a holiday rental in Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bennington. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family getaway.