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Find Hotels in Windsor, VT

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Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
The price is $162 per night from Oct 4 to Oct 4
19.79 mi from city center
3.9/5Good! (985 reviews)
"Beautiful space, undergoing some renovation so look forward to visiting again when it is finished!"

Reviewed on Aug 31, 2021

Killington Mountain Lodge, Tapestry Collection by Hilton
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
The price is $244 per night from Sep 22 to Sep 22
9.84 mi from city center
4.3/5Excellent! (353 reviews)
"Great location and easy parking. Nicely decorated."

Reviewed on Sep 17, 2021

The Shire Woodstock
Beautiful home offering privacy on 7 acres with sledding hill and private pond
5/5Exceptional! (6 reviews)
Lovely Property
"A beautiful spot in Vermont for a get away. The house has plenty of room and the property is quite large with a pond, firepit, open fields and places to hang out. Would definitely recommend."

Reviewed on Sep 4, 2021

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Beautiful home offering privacy on 7 acres with sledding hill and private pond
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Snowed Inn
3.5 out of 5
104 Miller Brook Road, Killington, VT
The price is $132 per night from Oct 19 to Oct 19
20.15 mi from city center
4.4/5Wonderful! (290 reviews)
"The property was very cute and clean. The staff was very attentive and accommodating."

Reviewed on Sep 14, 2021

Snowed Inn
Mountain Sports Inn
2 out of 5
813 Killington Road, Killington, VT
Fully refundableReserve now, pay when you stay
The price is $79 per night from Sep 20 to Sep 20
20.84 mi from city center
4.3/5Excellent! (292 reviews)
"very clean, quite,and very well priced"

Reviewed on Sep 17, 2021

Mountain Sports Inn
506 On the River Inn
4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is $339 per night from Sep 22 to Sep 22
9.64 mi from city center
4.7/5Exceptional! (598 reviews)
"Beautiful property and very comfortable beds. Pool was a little cold but the sauna and the whirlpool were good. Decent breakfast."

Reviewed on Aug 21, 2021

506 On the River Inn
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
9.74 mi from city center
4.6/5Wonderful! (292 reviews)
"Only breakfast option was a buffet that was lacking in food choices and $39."

Reviewed on Sep 16, 2021

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Woodstock Inn & Resort
Sunset Motor Inn
2 out of 5
305 North Main Street, West Lebanon, NH
Fully refundableReserve now, pay when you stay
The price is $99 per night from Sep 29 to Sep 29
14.55 mi from city center
3.3/5 (636 reviews)
"A basic motel that is clean, quiet, with a friendly staff and a decent continental breakfast buffet. We paid a small up charge for a river view room, which was an incredible bargain. The view was spectacular and elevated this motel to a resort."

Reviewed on Sep 6, 2021

Sunset Motor Inn
Norwich Inn
3 out of 5
325 Main St, Norwich, VT
Fully refundableReserve now, pay when you stay
The price is $259 per night from Oct 17 to Oct 17
16.86 mi from city center
4.6/5Wonderful! (198 reviews)
"The entire staff at the Inn made us feel like family!"

Reviewed on Aug 21, 2021

Norwich Inn
Super 8 by Wyndham White River Junction
2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is $104 per night from Oct 17 to Oct 17
11.8 mi from city center
3.2/5 (985 reviews)
"It was convenient and economical. Great price. A little out dated but that’s all we didn’t like about it."

Reviewed on Sep 13, 2021

Super 8 by Wyndham White River Junction
Windsor Mansion Inn
3.5 out of 5
153 Pembroke Road, Windsor, VT
The price is $152 per night from Sep 21 to Sep 21
2.57 mi from city center
4.6/5Wonderful! (201 reviews)
"What a unique and truly special property!! This mansion transports you back to the era of Great Gatsby in the beautiful setting of VT."

Reviewed on Sep 8, 2021

Windsor Mansion Inn
Best Western West Lebanon-Hanover Hotel
2.5 out of 5
45 Airport Road, West Lebanon, NH
Fully refundableReserve now, pay when you stay
The price is $149 per night from Sep 26 to Sep 26
11.53 mi from city center
4.3/5Excellent! (155 reviews)
"The rooms were recently redone and are beautiful. The breakfast was one of the best I have had a hotel of this type. The staff especially Tonya and the morning person were so friendly. They were warm and friendly. Lobby was not large but fine. I would happily stay again. It was higher priced than ..."

Reviewed on Sep 12, 2021

Best Western West Lebanon-Hanover Hotel
White River Inn and Suites
2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundable
The price is $105 per night from Oct 17 to Oct 17
11.76 mi from city center
3.7/5Good! (816 reviews)
"Wish they had a continental breakfast."

Reviewed on Jul 31, 2021

White River Inn and Suites
Hotel Coolidge
3 out of 5
39 South Main Street, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is $129 per night from Sep 23 to Sep 23
12.51 mi from city center
3.8/5Good! (532 reviews)
Great
"Lovely"

Reviewed on Sep 15, 2021

Hotel Coolidge
Fat Sheep Farm & Cabins
3 out of 5
122 Best Rd, Windsor, VT
3.39 mi from city center
4.3/5Excellent! (3 reviews)
"The cabin was perfect, roomy and clean. My 5 & 7 year old grandchildren loved that they could sled right next to the cabin. They also enjoyed helping to feed the sheep & chickens in the morning! We will definitely visit again during the summer to enjoy some of the area hiking!"

Reviewed on Mar 5, 2021

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Fat Sheep Farm & Cabins
Sunapee Lake Lodge
2.5 out of 5
1403 Route 103, Newbury, NH
Fully refundableReserve now, pay when you stay
The price is $139 per night from Sep 21 to Sep 21
21.84 mi from city center
4.1/5Very Good! (316 reviews)
"Very clean, up to date--appreciated mini frig. and microwave. Close to State Park beach."

Reviewed on Sep 6, 2021

Sunapee Lake Lodge
Six South St Hotel
2.5 out of 5
6 South Street, Hanover, NH
Fully refundableReserve now, pay when you stay
The price is $242 per night from Sep 26 to Sep 26
16.37 mi from city center
4.6/5Wonderful! (440 reviews)
"Very nice rooms. Friendly staff"

Reviewed on Sep 5, 2021

Six South St Hotel
Hanover Inn Dartmouth
4 out of 5
Two East Wheelock Street, Hanover, NH
Fully refundableReserve now, pay when you stay
The price is $299 per night from Sep 20 to Sep 20
16.5 mi from city center
4.8/5Exceptional! (484 reviews)
"Wonderful historic Inn on the Green in Hanover. It has been updated and is very nice. Beautiful furnishings and comfortable beds. A little bit of luxury at fairly reasonable rates. Less than the Woodstock inn, which is comparable. Walk a few steps to Dartmouth campus."

Reviewed on Sep 8, 2021

Hanover Inn Dartmouth
Jackson Gore Village
3 out of 5
111 Jackson Gore Road, Ludlow, VT
14.31 mi from city center
4.2/5Excellent! (466 reviews)
"We were looking for a quiet hotel with a resort atmosphere. Unfortunately, with the rain from Henri we weren't able to enjoy the Adventure Zone. (Plus, it's not cheap!) But the Inn was very nice -- clean and comfortable. We would definitely stay here again on our next trip to Ludlow."

Reviewed on Aug 24, 2021

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Jackson Gore Village
Snapdragon Inn
3.5 out of 5
26 Main Street, Windsor, VT
3.12 mi from city center
4.7/5Exceptional! (17 reviews)
"The history of the house is provided. Beutiful house and grounds."

Reviewed on Aug 4, 2019

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Snapdragon Inn
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Visiting Windsor

Visitors can enjoy all that Windsor has to offer including the breweries, golf courses, and forests. The scenic and rural setting also entices those visiting the city. Top sights around the area include Okemo Mountain Resort and Killington Resort.

  • You'll find 587 Expedia hotels and other accommodations in the larger area of Central Vermont- Killington
  • The closest major airport is in Lebanon, NH (LEB-Lebanon Municipal), 11.2 mi (18 km) from the city center
  • The next closest is in Springfield, VT (VSF-Hartness State), 11.4 mi (18.3 km) away

Sightseeing and Staying in Windsor

Favorite places to visit in the city include Path of Life Garden, Old Constitution House, and South Congregational Church. A couple of additional sights to add to your agenda are American Precision Museum and Mt Ascutney State Park.

As you plan your holiday getaway, you'll find 5 hotels and other lodging accommodations to choose from in Windsor. This is a top place to stay based on our user reviews:

  • Windsor Mansion Inn - With a stay at this 3.5-star bed & breakfast, guests can enjoy access to free breakfast and free parking, along with free WiFi. It's a favorite with Expedia travelers for its family-friendly amenities and breakfast.

In the surrounding area, popular places to visit include Okemo Mountain Resort, located 15 mi (24.2 km) from the heart of the city, and Killington Resort, which is 19.5 mi/31.4 km away.

Getting Around Windsor

To venture out into the surrounding area, hop on a train at Windsor Station. Windsor may not have many public transportation choices so consider a car rental to maximize your time.

Dressing for Windsor

  • Between January and March, you can expect average temperatures of 50°F during the day and 8°F at night
  • From April to June, the average during the day is 81°F, while the average at night is 28°F
  • July through September has daytime averages of 83°F with nighttime averages of 42°F
  • In October-December, you can expect daytime averages of 66°F and nighttime averages of 11°F
  • About 37.95 inches of rain falls on Windsor each year
  • Usually July and August are the hottest months with an average of 81°F, whereas January and February are often coldest, averaging 11°F

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