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Top cities in Cheshire County

Keene

Rindge

Jaffrey

West Chesterfield

Walpole

Swanzey

Fitzwilliam
Hinsdale

Chesterfield
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Our top choices for Cheshire County apartments




1. Lakefront Orange Vacation Rental - Pet Friendly!
Lakefront Orange Vacation Rental - Pet Friendly!Orange
10.0 out of 10, Exceptional, (33 reviews)
10/10
Exceptional
(33 reviews)
"It’s a wonderful place to stay!!"
"It’s a wonderful place to stay!!"Lori




2. 3-bedroom Proctorsville apartment, 10 min from Okemo, on Black River, great view
3-bedroom Proctorsville apartment, 10 min from Okemo, on Black River, great viewCavendish
9.2 out of 10, Wonderful, (7 reviews)
9.2/10
Wonderful
(7 reviews)
"Great home, very close to the resort and lots to do and eat near by!"
"Great home, very close to the resort and lots to do and eat near by!"karlie j.




3. Peaceful Mountain View Retreat
Peaceful Mountain View RetreatHancock
9.6 out of 10, Exceptional, (19 reviews)
9.6/10
Exceptional
(19 reviews)
"Very rustic 2nd floor. Clean and wonderful hosts. Recommend for those who don’t mind rustic atmosphere"
"Very rustic 2nd floor. Clean and wonderful hosts. Recommend for those who don’t mind rustic atmosphere"Glenda




4. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near BerkshiresGreenfield
9.4 out of 10, Exceptional, (11 reviews)
9.4/10
Exceptional
(11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
"Very satisfied with the stay . Clean quiet and relaxing stay."JAMES S.
The price is AED 327
AED 327
AED 841 total
includes taxes & fees
18 Nov - 19 Nov




5. Quiet Neighborhood, Perfect for Bird Lovers
Quiet Neighborhood, Perfect for Bird LoversSouth Deerfield
10.0 out of 10, Exceptional, (53 reviews)
10/10
Exceptional
(53 reviews)
"Wonderful location. Great host!!"
"Wonderful location. Great host!!"Rebecca K.




6. Revitalized Firehouse Retreat in Downtown Shelburne Falls. Walk to Everything!
Revitalized Firehouse Retreat in Downtown Shelburne Falls. Walk to Everything!Shelburne Falls
10.0 out of 10, Exceptional, (14 reviews)
10/10
Exceptional
(14 reviews)
"Our stay at the revitalized firehouse retreat was wonderful! It was in a great location in downtown Shelburne Falls and check-in was easy. The unit was very clean and offered all the amenities we needed. We look forward to returning soon!"
"Our stay at the revitalized firehouse retreat was wonderful! It was in a great location in downtown Shelburne Falls and check-in was easy. The unit was very clean and offered all the amenities we needed. We look forward to returning soon!"diana




7. Mount Snow Best View - Sauna|HotTub|Pool|Fireplace
Mount Snow Best View - Sauna|HotTub|Pool|FireplaceWest Dover
10.0 out of 10, Exceptional, (11 reviews)
10/10
Exceptional
(11 reviews)
"Great location. House was clean. Family had a great time."
"Great location. House was clean. Family had a great time."Daniel C.




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
9.8 out of 10, Exceptional, (49 reviews)
9.8/10
Exceptional
(49 reviews)
"Wonderful stay! Amazing location!"
"Wonderful stay! Amazing location!"Basmattee B.
The price is AED 320
AED 320
AED 594 total
includes taxes & fees
30 Nov - 1 Dec




9. Lakeside Spofford Retreat Near Hiking & Boating!
Lakeside Spofford Retreat Near Hiking & Boating!Spofford
9.0 out of 10, Wonderful, (2 reviews)
9.0/10
Wonderful
(2 reviews)
"There is a very clear view of the lake. However it is not easy to find access because of the surrounding private lake access points. We did see a bald eagle flying low over the beautiful lake."
"There is a very clear view of the lake. However it is not easy to find access because of the surrounding private lake access points. We did see a bald eagle flying low over the beautiful lake."Carol O




10. Light-filled treetop apartment close to downtown Greenfield and Highland Park
Light-filled treetop apartment close to downtown Greenfield and Highland ParkGreenfield
9.8 out of 10, Exceptional, (13 reviews)
9.8/10
Exceptional
(13 reviews)
"Nice place"
"Nice place"Tom
The price is AED 826
AED 826
AED 1,001 total
includes taxes & fees
17 Nov - 18 Nov
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.
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.
Top reviews in Cheshire County




Vikings Villages Resort
Vikings Villages ResortGuilford
10/10 Excellent
I would leave all my possessions behind to live in this cabin forever.
I would leave all my possessions behind to live in this cabin forever.
Diego




Centennial House
Centennial HouseNorthfield
10/10 Excellent
My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne
My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne
Anonymous traveler




Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection HotelWest Chesterfield
10/10 Excellent
Everybody there was very pleasant. The entire building is immaculate. Wonderful peaceful setting on the Connecticut River.
Everybody there was very pleasant. The entire building is immaculate. Wonderful peaceful setting on the Connecticut River.
James




The Carriage Barn Inn
The Carriage Barn InnKeene
10/10 Excellent
Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++
Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++
Richard




Chesterfield Inn
Chesterfield InnWest Chesterfield
10/10 Excellent
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Beverly




Hampton Inn & Suites Keene
Hampton Inn & Suites KeeneKeene
10/10 Excellent
The staff are among the kindest people I’ve ever encountered at a hotel. Simply amazing
The staff are among the kindest people I’ve ever encountered at a hotel. Simply amazing
kristin




Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection HotelKeene
10/10 Excellent
Friendly staff and clean, spacious room. Breakfast was very good!!
Friendly staff and clean, spacious room. Breakfast was very good!!
Kristine




Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene DowntownKeene
10/10 Excellent
Everything about this hotel was good. The staff, the room, and the location were all great.
Everything about this hotel was good. The staff, the room, and the location were all great.
Vic




Best Western Plus Keene Hotel
Best Western Plus Keene HotelKeene
10/10 Excellent
Professional staff. Clean & attractive.
Some quests noisy in halls tho.
Professional staff. Clean & attractive.
Some quests noisy in halls tho.
Susan




Monadnock Inn
Monadnock InnJaffrey
10/10 Excellent
On a Foliage tour through New England in October, my wife and I stayed at The Monadnock Inn following a hike of the nearby Mt. Monadnock. Arrival mid-week was simple and the Inn is full of centuries-old charm and comfort. Check-in was very simple and we were handed a key and walked up the stairs to the 3rd Floor Pauline Room. The room was very cozy with an antique soak tub and shower (great after a long hike), beautiful bay windows, steam radiator, comfortable bed, and warmly lit. There was no...
On a Foliage tour through New England in October, my wife and I stayed at The Monadnock Inn following a hike of the nearby Mt. Monadnock. Arrival mid-week was simple and the Inn is full of centuries-old charm and comfort. Check-in was very simple and we were handed a key and walked up the stairs to the 3rd Floor Pauline Room. The room was very cozy with an antique soak tub and shower (great after a long hike), beautiful bay windows, steam radiator, comfortable bed, and warmly lit. There was no...
Todd




Harvest Barn Inn
Harvest Barn InnBellows Falls
10/10 Excellent
It was a perfect stay. The room was clean, the view beautiful and the breakfast was wonderful. I wish e could have stayed longer!
It was a perfect stay. The room was clean, the view beautiful and the breakfast was wonderful. I wish e could have stayed longer!
Virginia




Inn on Putney Road
Inn on Putney RoadBrattleboro
10/10 Excellent
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Victoria




Four Columns Inn
Four Columns InnNewfane
10/10 Excellent
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
Nettie




Colonel Williams Inn
Colonel Williams InnBrattleboro
10/10 Excellent
Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...
Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...
Ann




Shelburne Springs Hotel
Shelburne Springs HotelShelburne Falls
10/10 Excellent
We travelled for one night and it’s a gem. Spacious, easy in and out. Very comfortable.
We travelled for one night and it’s a gem. Spacious, easy in and out. Very comfortable.
Brian




The Maguire House Bed & Breakfast
The Maguire House Bed & BreakfastAshburnham
10/10 Excellent
The view from the deck was amazing. It overlooked a lake and Mount Monadanock. Our room was spacious and clean. The hosts were lovely people. They had a refrigerator stocked with wine and beer and they put out cookies in the afternoon. Breakfast was delicious and on the morning we had to leave before breakfast, they packed some bread and fruit for us.
The view from the deck was amazing. It overlooked a lake and Mount Monadanock. Our room was spacious and clean. The hosts were lovely people. They had a refrigerator stocked with wine and beer and they put out cookies in the afternoon. Breakfast was delicious and on the morning we had to leave before breakfast, they packed some bread and fruit for us.
Anonymous traveler
