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Browse Select Chesterfield Guest Houses

The Black Bear Lodge at Stratton Mountain Resort
Indoor spa tub

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
7.6 out of 10, Good, (881)
"Wonderful Lodge style place. Rustic and humble but very well priced with standard amenties and great location"
The price is CA $257
CA $311 total
includes taxes & fees
Jan 20 - Jan 21
The Black Bear Lodge at Stratton Mountain Resort
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (371)
"Great location. Bare minimum facilities but that’s expected considering the price. Good value for money. No breakfast. Earlier reviews mentioned breakfast. Did late check in but the instructions were very clear. "
The price is CA $206
CA $250 total
includes taxes & fees
Jan 20 - Jan 21
Mountaineer Inn
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1003)
"Like size of room"
The price is CA $141
CA $155 total
includes taxes & fees
Jan 12 - Jan 13
Colonial Motel And Spa
Hampton Inn Brattleboro
Lobby

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (1000)
"The hotel was clean and staff were helpful. The breakfast was better than average and they have 24 hours hot coffee and tea. The pool and hot tub were closed which was a disappointment. A pipe burst in our bathroom in the middle of the night, but the staff were quick to get us a new room and were credited for a nights stay. Overall, a good place to stay in the area. "
The price is CA $147
CA $162 total
includes taxes & fees
Jan 12 - Jan 13
Hampton Inn Brattleboro
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (172)
"👍"
The price is CA $402
CA $482 total
includes taxes & fees
Jan 22 - Jan 23
Mount Snow Grand Summit Resort
The Covered Bridge Inn
Concierge desk

The Covered Bridge Inn

2.5 star property
8.0 out of 10, Very good, (1000)
"Everything is right there I mean literally everything was right there"
The price is CA $168
CA $185 total
includes taxes & fees
Feb 8 - Feb 9
The Covered Bridge Inn
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"The check in staff was very friendly. We arrived late in the evening. Room was clean and quiet. It was a last minute stay before heading to a ski hill. It worked out well for the price. "
The price is CA $134
CA $146 total
includes taxes & fees
Jan 9 - Jan 10
The Putney Inn
Red Roof Inn PLUS+ South Deerfield – Amherst
Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 star property
7.2 out of 10, Good, (1000)
"Clean room and it served the purpose of the stay"
The price is CA $129
CA $145 total
includes taxes & fees
Jan 14 - Jan 15
Red Roof Inn PLUS+ South Deerfield – Amherst
The Upper Pass Lodge at Magic Mountain
Restaurant

The Upper Pass Lodge at Magic Mountain

2.5 star property
8.4 out of 10, Very good, (614)
"This is a dog friendly place so a good place for family trip with a dog. Easy to access from parking to a room using a door facing to parking so we can load and unload staffs. Having a nice restaurant for dinner but need to make a reservation in advance. Foods are good and not overpriced."
The price is CA $141
CA $155 total
includes taxes & fees
Jan 15 - Jan 16
The Upper Pass Lodge at Magic Mountain
Chalet 239
Family Room | Living area

Chalet 239

2.0 star property
9.4 out of 10, Exceptional, (51)
"Very nice accommodation for a short ski trip. Modern updates and clean room. The owners and the other guests were friendly. "
The price is CA $229
CA $252 total
includes taxes & fees
Jan 22 - Jan 23
Chalet 239
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Interior

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

10.0 out of 10, Exceptional, (144)
"I can unequivocally say we had a wonderful time from the moment we drove up until we were driving away. We had booked this as a surprise for our adult children (and their partners) to stay with us. They were absolutely wowed by the amazing castle, the amazing views and just how cool it was. The caretaker Mike was incredibly helpful and helped get us set up perfectly. We would 100% stay again - if we could find an opening :-) "
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (688)
"Very cool place. Super retro. Loved the record players and records everywhere. And it smells like popcorn, always."
The price is CA $164
CA $181 total
includes taxes & fees
Jan 16 - Jan 17
Latchis Hotel
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1002)
"Lovely staff"
The price is CA $218
CA $237 total
includes taxes & fees
Jan 16 - Jan 17
Courtyard by Marriott Keene Downtown
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (547)
"Price and quality makes it great "
The price is CA $148
CA $163 total
includes taxes & fees
Jan 12 - Jan 13
Comfort Inn & Suites Brattleboro I-91
Hampton Inn & Suites Greenfield
Room, 2 Queen Beds, Non Smoking

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (767)
"Staff was very friendly and accommodating. Despite some current renovation work, property was clean and quiet."
The price is CA $194
CA $217 total
includes taxes & fees
Jan 26 - Jan 27
Hampton Inn & Suites Greenfield
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (978)
"Clean comfy room:)"
The price is CA $132
CA $143 total
includes taxes & fees
Jan 16 - Jan 17
Days Inn by Wyndham Keene NH
Best Western Springfield Hotel
Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed)

Best Western Springfield Hotel

2.5 star property
8.8 out of 10, Excellent, (733)
"Quick and easy check in. Clean room. Good price. Decent amenetied in hotel. Would stay again when in area."
The price is CA $218
CA $238 total
includes taxes & fees
Jan 20 - Jan 21
Best Western Springfield Hotel
Black Mountain Inn
Front of property

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (424)
"Staff were great and very kind. Property is clean and nice. Definitely would recommend "
The price is CA $147
CA $162 total
includes taxes & fees
Jan 22 - Jan 23
Black Mountain Inn
Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
Exterior

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (953)
"Place is clean, safe, well lit, plenty of parking, friendly and helpful staff, and breakfast is included. Would stay again, highly recommend. "
The price is CA $207
CA $228 total
includes taxes & fees
Feb 2 - Feb 3
Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (274)
"Nice simple and modern. Great customer service. Check in and out was simple and quick. Unfortunately pool wasnt open but guests where advised the Best Western across the way was allowing their guests to show room cards to be able to use the pool their facility. Clean rooms but no laundry amenities available. Had a great stay. But whiling using the side door my wife notcied the levels on the walk way were not defined and walking thru at night time could create an emergency for another guest....
The price is CA $195
CA $212 total
includes taxes & fees
Jan 26 - Jan 27
Hampton Inn & Suites Keene
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 Chesterfield

Charming Waterfront Log Cabin
3 bedrooms, travel crib, free WiFi, bed sheets

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
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Hilltop Home with Great Views
Interior

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views
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.