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Search Guest Houses in Winchester

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Compare Guest Houses in Winchester with updated reviews, rates, and availability.

Great Wolf Lodge Boston / Fitchburg, MA

3.5 star property
8.4 out of 10, Very Good, (884)
"Perfect place for families with young kids :)"
The price is AED 657
AED 875 total
includes taxes & fees
10 Feb - 11 Feb
Great Wolf Lodge Boston / Fitchburg, MA

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (407)
"Food choice limited for continental breakfast. staff friendly. pool table had torn felt and 2 sets of balls."
The price is AED 590
AED 715 total
includes taxes & fees
12 Feb - 13 Feb
Mountaineer Inn

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
7.6 out of 10, Good, (891)
"The place was very nice but a little dated"
The price is AED 657
AED 796 total
includes taxes & fees
2 Mar - 3 Mar
The Black Bear Lodge at Stratton Mountain Resort

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (178)
"Older, air drying in the locker rooms odd . Moisture. "
The price is AED 1,029
AED 1,231 total
includes taxes & fees
10 Mar - 11 Mar
Mount Snow Grand Summit Resort

The Colonial Hotel

3.0 star property
8.6 out of 10, Excellent, (1002)
"Great restaurant in the hotel nice hot tub! "
The price is AED 514
AED 574 total
includes taxes & fees
10 Feb - 11 Feb
The Colonial Hotel

Doubletree by Hilton Hotel Leominster

4.0 star property
8.6 out of 10, Excellent, (1001)
"."
The price is AED 482
AED 538 total
includes taxes & fees
16 Feb - 17 Feb
Doubletree by Hilton Hotel Leominster

Big Bears Lodge

3.0 star property
9.0 out of 10, Wonderful, (169)
"very friendly"
The price is AED 612
AED 674 total
includes taxes & fees
9 Feb - 10 Feb
Big Bears Lodge

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1002)
"Like the fact that your room is private some creeping to the floors otherwise simple and does the job great never tried the spa closed Sunday at 5"
The price is AED 400
AED 440 total
includes taxes & fees
9 Feb - 10 Feb
Colonial Motel And Spa

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1002)
"The Putney Inn was perfect for an easy overnight in Vermont. Rate was reasonable and room was clean. The location was extremely convenient, right off the highway. We would stay again if we were in the area!"
The price is AED 326
AED 356 total
includes taxes & fees
10 Feb - 11 Feb
The Putney Inn

Chalet 239

2.0 star property
9.4 out of 10, Exceptional, (56)
"Place is very new. House keeper should give little details to the inside refrigerator. Little filthy "
The price is AED 680
AED 749 total
includes taxes & fees
3 Mar - 4 Mar
Chalet 239

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (577)
"This was a very convenient location from the highway (91), gas, and dinner at Ninety-Nine, located immediately adjacent. Breakfast had limited, but good options, including hot choices, fresh fruit, multiple coffee and tea selections. Do recommend."
The price is AED 380
AED 418 total
includes taxes & fees
9 Mar - 10 Mar
Comfort Inn & Suites Brattleboro I-91

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very Good, (1001)
"Check in staff were super helpful. We did not know the hot tub and pool were not open, which bummed us out. We loved that all the rooms were animal friendly. The cookies were also Faboo!"
The price is AED 378
AED 415 total
includes taxes & fees
11 Mar - 12 Mar
Hampton Inn Brattleboro

Comfort Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Very clean and great location for a quick Uber to events at UMass Amherst."
The price is AED 465
AED 520 total
includes taxes & fees
10 Feb - 11 Feb
Comfort Inn & Suites

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (592)
"This is my second stay at The Ellery. The staff is great and the property is very clean. It’s close to Smith and a few minutes to Main Road. "
The price is AED 511
AED 570 total
includes taxes & fees
9 Feb - 10 Feb
The Ellery

Best Western Springfield Hotel

2.5 star property
8.8 out of 10, Excellent, (740)
"Very nice hotel, close to okemo. Nice breakfast! "
The price is AED 592
AED 645 total
includes taxes & fees
9 Mar - 10 Mar
Best Western Springfield Hotel

Fullerton Inn

2.5 star property
8.0 out of 10, Very Good, (324)
"This is a lovely old building with a lot of character and charm. We were greeted upon arrival and given all the information we needed for parking in the back lot due to snow plowing. The room was small, which was fine and what we had reserved, no complaints there. We had a double bed and it was very, very soft if you like that sort of thing. There was some draftiness in the second floor end room we stayed in, and the heat was not running when we got there, which was an issue for an hour or two...
The price is AED 474
AED 516 total
includes taxes & fees
2 Mar - 3 Mar
Fullerton Inn

Austrian Haus Lodge

2.5 star property
8.6 out of 10, Excellent, (47)
"Great stay weather caused slippery driveway "
Austrian Haus Lodge

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!

Inn on Boltwood

3.0 star property
9.4 out of 10, Exceptional, (625)
"Friendly staff and great location. Rooms and furnitures need updating. Shower pressure was too high and couldn’t be adjusted. Room door latch and lock were broken (service call was made but no one came to fix it). "
The price is AED 658
AED 735 total
includes taxes & fees
12 Feb - 13 Feb
Inn on Boltwood

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (704)
"I love staying at the Latchis, particularly because of its location right on Main St., giving it proximity to great food, a wide variety of stores, the art museum, the train station and transportation center, it's attached lovely historic cinema which always shows quality films, the food co-op, the historic town hall, the community center, the large well-socked local library, and the totally unique concept of having a record player in every room with plenty of vinyl! "
The price is AED 456
AED 502 total
includes taxes & fees
2 Mar - 3 Mar
Latchis Hotel
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 Winchester

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

6.8 out of 10, (13)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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.