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Compare 28 Cottages in Bennington with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (14)
"The property is lovely. It suited our needs and fully equipped. "
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Cozy cottage on Pleasant Pond

9.6 out of 10, Exceptional, (19)
"Stayed in the winter, place got a bit cold (it does not have central heat). Wasn’t a lighter or enough firewood for our stay but the host brought a lighter and more wood. Beautiful pond in the back and the location is good, with easy access to the highway. Neighbors were close by, we were asked to turn off the outdoor light because it was shining into their house. Cottage was clean. There are security cameras outside. Overall it is a cozy place to stay in a good area. "
Cozy cottage on Pleasant Pond

Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself

9.6 out of 10, Exceptional, (18)
"Our kids said the beds were the most comfortable beds they'd ever slept on, with the coziest blankets. The cabin was warm, cozy, and homey. Host was very nice and communication was timely and helpful. Beautiful view on the lake. Close to all amenities, shopping, and grocery stores."
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself

Quaint Dunbarton Waterfront Cottage

9.2 out of 10, Wonderful, (45)
"Bright & clean. Gorgeous location on the water with your own little pier. Simply such a serene place to have morning coffee. "
Quaint Dunbarton Waterfront Cottage

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

10.0 out of 10, Exceptional, (28)
"This pearl of an oasis is on Pearly Pond with a breath-taking view of Mount Watchusett. Nestled in a quiet cove, it is still close to local amenities, trails and restaurants. The cabin has everything a person could image to bring on vacation such as nice cookware, beach towels, and games. The home boasts a lovely screened in porch and a beautiful dock with canoe and kayak. We highly recommend this cabin. Gary and Linda are consumate hosts!!"
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Lakefront Bradford Cottage w/ Dock, Near Skiing!

9.4 out of 10, Exceptional, (6)
"The cottage has a nice setting on the narrow end of Lake Todd. The kitchen was well stocked with kitchen utensils. Would stay here again."
Lakefront Bradford Cottage w/ Dock, Near Skiing!

Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!

9.0 out of 10, Wonderful, (38)
"Almost every window had a crack or a hole, patched only with clear tape. Some windows had no panes, just the storm windows to keep out weather. The "queen" bed is an uncomfortable full mattress on a queen frame - that's squeaks horribly every time you move. The couch bed was also very uncomfortable. The previous guests did not follow the checkout procedure and no one else ever fixed it b/c there was hair on the pillowcases when I arrived, indicating the beds were slept in and not remade with...
Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!

Charming Jaffrey Cottage w/ Deck & Grill!

10.0 out of 10, Exceptional, (39)
"Stayed four nights. Perfect weather and the foliage was fabulous.The cottage was ideal for us. Tastefully decorated and everything labeled. Wish we lived closer so we could go again in other seasons."
Charming Jaffrey Cottage w/ Deck & Grill!

Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

3.0 star property
Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

Luxe Riverfront Cottage w/ Dock by Lake Horace!

7.8 out of 10, Good, (7)
"Glad there was air conditioning didn’t realize until we arrived so website listing should be updated."
Luxe Riverfront Cottage w/ Dock by Lake Horace!

Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

9.6 out of 10, Exceptional, (4)
"This lake house has it all. Views, nature, wildlife and so many things to do. Kayak, paddleboard, fishing, boating and so much more! Highly recommend! The host is top notch! "
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

Cozy Tiny House on Main Street. Fully Renovated.

10.0 out of 10, Exceptional, (4)
"I was in Dublin visiting my daughter who goes to high school here and it was the perfect place for me to stay and she stayed with me two nights. The owner thought of everything you would need. It was super clean and everything looked brand new. Really well decorated. The owner was super helpful and I’m sure I’ll be back before my girl graduates. Highly recommend!"
The price is SAR 661
SAR 1,014 total
includes taxes & fees
30 Dec - 31 Dec
Cozy Tiny House on Main Street. Fully Renovated.

Lakefront Bradford Cottage w/ Dock, Near Skiing!

3.0 star property
Lakefront Bradford Cottage w/ Dock, Near Skiing!

Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!

3.0 star property
Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!

The Cozy Cottage

10.0 out of 10, Exceptional, (4)
"The cottage was exactly what my family needed for our visit . Tucked off the road and very quiet. Dan responded immediately to me whenever I reached out. "
The Cozy Cottage

Charming Jaffrey Cottage w/ Deck & Grill!

3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!

Luxe Riverfront Cottage w/ Dock by Lake Horace!

3.0 star property
Luxe Riverfront Cottage w/ Dock by Lake Horace!

Historic Bradford Home - 8 Mi to Mount Sunapee!

3.0 star property
Historic Bradford Home - 8 Mi to Mount Sunapee!

Cottage Lake Nubanusit

10.0 out of 10, Exceptional, (2)
"A lovely patina from years of caring use, authentic, genuine, simple and very comfortable. Well equipped, everything works. Screen porch is perfect. Dock and shoreline easy and very pretty, perfect for kayaks/canoes. We look forward to a future stay!"
Cottage Lake Nubanusit

Beautiful Modern Cottage with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was our 2nd stay with the host. Everything was perfect and relaxing. "
The price is SAR 635
SAR 1,116 total
includes taxes & fees
6 Jan - 7 January 2025
Beautiful Modern Cottage with Sauna on Lake Monomonac
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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Other property types in Bennington

Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.

10.0 out of 10, Exceptional, (57)
"We thoroughly enjoyed our recent stay at this beautifully restored 257 year old farmhouse. The location was peaceful and private — truly an unexpected gem within minutes of the center of New Hampshire’s capital city. During our stay we experienced two snowstorms and we were grateful for our host’s balance of respecting our privacy while also ensuring us safe access in and out of the snowy property. We can’t wait to return in June and again in September! "
Reuben Dimond House, Renovated Historic Farmhouse in the Capital, Concord, NH.

Rustic Waterfront Cottage w/ Fire Pit & Kayaks

2.5 star property
Rustic Waterfront Cottage w/ Fire Pit & Kayaks

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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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