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Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Bennington vacation rentals

A conservatory with a view of a lake surrounded by trees. Inside, there are two sofas facing the glass walls.

1. Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Bennington
10.0 out of 10, Exceptional, (14 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
The price is CA $276
CA $546 total
includes taxes & fees
Sep 2 - Sep 3
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
A hot tub with a stone surround, wooden beams, and string lights.

2. Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Antrim
9.6 out of 10, Exceptional, (10 reviews)
The price is CA $248
CA $434 total
includes taxes & fees
Aug 30 - Aug 31
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
A cluster of white buildings with multiple chimneys, surrounded by lush green grass and trees with autumn foliage.

3. Room 10 - Queen Room

Room 10 - Queen Room
Francestown
10.0 out of 10, Exceptional, (1 review)
"Easy access to skiing Crotched mountain, great breakfast and dinner! Lovely people!"
United States
j l.
The price is CA $350
CA $433 total
includes taxes & fees
Sep 14 - Sep 15
Room 10 - Queen Room
A sandy beach area with a volleyball net and a ladder, overlooking a calm lake with trees in the background.

4. HotTub FirePit Games Huge Backyard Family Friendly

HotTub FirePit Games Huge Backyard Family Friendly
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 CA $248
CA $434 total
includes taxes & fees
Aug 30 - Aug 31
HotTub FirePit Games Huge Backyard Family Friendly
A hot tub with a stone surround, wooden beams, and string lights.

5. 16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
9.8 out of 10, Exceptional, (10 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 CA $497
CA $875 total
includes taxes & fees
Aug 30 - Aug 31
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
A cluster of white buildings with multiple chimneys, surrounded by lush green grass and trees with autumn foliage.

6. Spacious room with Queen bed and pullout couch - Dog Friendly!

Spacious room with Queen bed and pullout couch - Dog Friendly!
Francestown
10.0 out of 10, Exceptional, (1 review)
"This was a great place to stay for a family ski getaway to Crotchet Mountain. The whole establishment is small and quaint, with a few wings of guest bedrooms branching off of the main tavern/restaurant. But we didn’t feel like we were intruding on someone’s house, which is our main worry when staying at a Bed & Breakfast style inn. We have 2 young children, so we were concerned beforehand about being able to keep the kids contained from disrupting anyone else’s stay or making a mess in the...
United States
Jeremiah M.
The price is CA $434
CA $536 total
includes taxes & fees
Aug 31 - Sep 1
Spacious room with Queen bed and pullout couch - Dog Friendly!
A cluster of white buildings with multiple chimneys, surrounded by lush green grass and trees with autumn foliage.

7. 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 CA $417
CA $516 total
includes taxes & fees
Aug 31 - Sep 1
Room 08 - King Room - Handicap accessible
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

8. 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
10.0 out of 10, Exceptional, (41 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is CA $112
CA $227 total
includes taxes & fees
Sep 2 - Sep 3
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A modern living room with a fireplace, a mounted TV, and a leather couch.

9. 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, (25 reviews)
"I would stay here again."
United States
Ann M.
The price is CA $191
CA $320 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Cabin in a Rural Setting #16 near Temple,NH
A kitchen with a brick fireplace, wooden cabinets, a central island with stools, and a large window with plants.

10. Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Dublin
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is CA $582
CA $1,010 total
includes taxes & fees
Aug 30 - Aug 31
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

11. Cozy Cabin in a rural setting #12 in Temple NH

Cozy Cabin in a rural setting #12 in Temple NH
Temple
9.2 out of 10, Wonderful, (21 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is CA $139
CA $256 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Cabin in a rural setting #12 in Temple NH
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

12. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is CA $291
CA $439 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Tiny House on Main Street. Fully Renovated.
A black-framed door with a glass panel, leading into a hallway with wooden flooring and white walls.

13. Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.2 out of 10, Wonderful, (10 reviews)
"Place was a very nice stay, area was close to nice places."
United States
Rui V.
The price is CA $175
CA $279 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Cabin in a Rural setting-14
A stone pathway leading to a large, multi-story building surrounded by trees and shrubs.

14. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (21 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is CA $222
CA $400 total
includes taxes & fees
Sep 1 - Sep 2
Cottage beside a waterfall
A cluster of white buildings with multiple chimneys, surrounded by lush green grass and trees with autumn foliage.

15. Room 02 - Queen & Twin Room

Room 02 - Queen & Twin Room
Francestown
The price is CA $417
CA $516 total
includes taxes & fees
Aug 31 - Sep 1
Room 02 - Queen & Twin Room
A stone pathway leading to a rustic building with a steep roof, surrounded by autumn foliage and a stone wall.

16. River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
10.0 out of 10, Exceptional, (6 reviews)
"Couldn't ask for a lovelier place to spend a couple of days in New Hampshire in May!"
United States
Bob H.
The price is CA $222
CA $400 total
includes taxes & fees
Sep 1 - Sep 2
River Room overlooking the waterfall
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is CA $467
CA $880 total
includes taxes & fees
Aug 31 - Sep 1
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

18. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is CA $234
CA $460 total
includes taxes & fees
Aug 30 - Aug 31
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A sunlit room with large windows, a bench, and a row of grey sofas.

19. 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, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is CA $243
CA $512 total
includes taxes & fees
Sep 8 - Sep 9
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
A house by a lake with a dock and a boat.

20. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is CA $273
CA $418 total
includes taxes & fees
Sep 6 - Sep 7
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Has everything necessary for a two night stay."
Giovanna 2-night trip
Posted 2 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Bennington

Everything you need to know about Bennington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bennington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Bennington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bennington. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bennington vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington vacation rentals we have selected for you start as low as CA $256 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bennington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private Beach And Mountain Lake Home: You might like this vacation home rental near Bennington. It is located on the beach 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. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Bennington?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Bennington stay.

What’s there to see and do in Bennington?

While exploring the area, visit family-friendly sights like Ava Marie Handmade Chocolates, 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.