Top Hotels in Windsor County

Explore Windsor County with stays near iconic landmarks, luxury hotels, and top boutiques for the best shopping and dining

Jackson Gore Village on Okemo Mountain
8.5 (101 reviews)

Jackson Gore Village on Okemo Mountain ★★★

📍 111 Jackson Gore Rd, Ludlow

"When we arrived, the front desk staff were very kind and welcoming. We were told we could eat at the restaurant right off the lobby so we planned to eat dinner there. When we arrived at the restaurant 20 mins later, they told us we could not eat there unless we had made prior reservations due to a wedding they had next door. The lady told us “we have to prioritize the wedding of 200 people”. I asked where we should eat and the lady shrugged. One of the waiters, who was very kind apologized and recommended the bar . They had some dishes from their restaurant menu. We were pretty irritated because we were both exhausted and the lady was very rude to us. We watched 20+ people get turned away from eating dinner due to this wedding. I completely understand that they need to focus on a wedding and the food for the wedding, however we should’ve been told about this when we arrived that the restaurant wasn’t available unless we had already made a reservation. The resort is very nice and there was a lot of fun things you can do there, but some of the staff were quite unkind."

The Jackson
9.6 (100 reviews)

The Jackson ★★★★

📍 43 Senior Lane, Woodstock

Main and Mountain
9.4 (43 reviews)

Main and Mountain ★★

📍 112 Main Street, Ludlow

"I really love this place. This was our second stay in the very comfortable Room 6. The king sized bed is unbelievably comfortable and the heat pump in the room works so well to keep the room whatever temperature you want. I like the remote check in; it works pretty well. Staff is extremely helpful if you have any issues."

The Hartness House
8.2 (70 reviews)

The Hartness House ★★★

📍 109 Front St, Springfield

Stone Hearth Inn and Eatery
9.1 (52 reviews)

Stone Hearth Inn and Eatery ★★

📍 698 Vermont 11, Chester

Woodstock Inn & Resort
9.3 (101 reviews)

Woodstock Inn & Resort ★★★★★

📍 14 The Grn, Woodstock

The Pointe at Castle Hill Resort & Spa
8.6 (101 reviews)

The Pointe at Castle Hill Resort & Spa ★★★

📍 2940 Route 103, Cavendish

"The hot tub was filthy"

Riverfront Home w/ Hot Tub Near Killington Resort
9.1 (1 reviews)

Riverfront Home w/ Hot Tub Near Killington Resort ★★★

📍 145 Mountainside Rd, Bridgewater

Hampton Inn White River Junction
8.5 (103 reviews)

Hampton Inn White River Junction ★★

📍 104 Ballardvale Dr, White River Junction, Hartford

"The room is very clean, the bed is very comfortable, there is a coin-operated washing machine on the second floor, and there are homemade waffles for breakfast. The key is to choose the flavor. I recommend friends to stay here!"

See All Hotels in Windsor County

Choose the Perfect Windsor County Stay for Your Travel Needs

The Inn at Weathersfield Hotels in Windsor County

The Inn at Weathersfield

"For the last 40 years, we have gone ( with friends) to various Inns in New England. We have found some gems and had an occasional mishap. This was not our best experience. To note, we are all in the over 75ys category, although still in great shape. We like not skiers/hikers. We like craft fairs and seeing the local sights. The Inn was purchased by 2 Bulgarian brothers (plus their families) about 5 years ago and is definitely showing signs of age. It was important to keep your eyes on the floor because there were different levels in the flooring and our friend fell going into his bathroom because there was a “step up” that he completely missed. When we arrived we were given our keys and asked what we wanted for breakfast on the next 2 mornings. The offerings were a veggie omelet or pancakes, both came with bacon/sausage & toast. There were no other choices ( no fruit, cereal, muffins, yogurt) Our room, at the top of a narrow, windy, narrow stairs was pleasant although the window AC was noisy. The bathroom had a small shower and jacuzzi. The shower that night was lukewarm and the towels were gym quality. We reported our lack of hot water and the owner said he would fix it. Dinner that night was average. Nice bar with lots of “special” alcohol. Owner served as the bartender. Waitress was lovely. Owner said the water issue was fixed It was quiet, although the sounds of cars could still be heard on the road. The Inn is a fair distance back, so that was surprising. I forgot my own pillow.. big mistake. Next morning, no hot water at all. Turns out bigger problem than previously thought and it needed a plumber. Told it would be fixed by the time we got back from the day’s outing Breakfast was not great. There was a coffee bar. Bacon was paper thin and toast was cold. Pancakes were soggy/cold. We left and spent a lovely day driving through Vermont, stopping at various craft fairs. We got back around 3p. Plumber hadn’t yet arrived and our room had not been cleaned. It turns out we have to ask for room service when you arrive otherwise it isn’t done. We are told that this is the way all the local Inns behave. We have never experienced this. Chalk it up to “new knowledge”. Plumber arrives at 4:30p and we have hot water!! Had dinner that night at Simon Pearce restaurant which was amazing. Wonderful food and service. Definately a winner. We left the next morning, anxious to be gone. The inn keeper did give us a voucher for a “free” night at our next visit as a compensation for the water issue. To be fair, our friends did not experience the same water issues, just the fall going into the bathroom. They had housekeeping come up and do their room at 3p when we got back. One of the few Inns I would not recommend…ever."

Deer Brook Inn Hotels in Windsor County

Deer Brook Inn

"Deer Brook Inn was amazing! It is beautifully decorated, immaculate and very cozy. Carmen and Chris were wonderful hosts. They were very accommodating, personable and hospitable. The inn is definitely a labor of love for them. Breakfasts were delicious and Carmen is an excellent baker. I highly recommend staying here when in the area."

Holiday Inn Club Vacations MOUNT ASCUTNEY RESORT by IHG Hotels in Windsor County

Holiday Inn Club Vacations MOUNT ASCUTNEY RESORT by IHG

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo Hotels in Windsor County

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

See all

Real Traveller Reviews of Windsor County Hotels

8.4
Excellent Community Rating
Real & verified guest reviews from all over the world
G

US Guest User

Couple
Jackson Gore Village on Okemo Mountain ★★★
"When we arrived, the front desk staff were very kind and welcoming. We were told we could eat at the restaurant right off the lobby so we planned to eat dinner there. When we arrived at the restaurant 20 mins later, they told us we could not eat there unless we had made prior reservations due to a wedding they had next door. The lady told us “we have to prioritize the wedding of 200 people”. I asked where we should eat and the lady shrugged. One of the waiters, who was very kind apologized and recommended the bar . They had some dishes from their restaurant menu. We were pretty irritated because we were both exhausted and the lady was very rude to us. We watched 20+ people get turned away from eating dinner due to this wedding. I completely understand that they need to focus on a wedding and the food for the wedding, however we should’ve been told about this when we arrived that the restaurant wasn’t available unless we had already made a reservation. The resort is very nice and there was a lot of fun things you can do there, but some of the staff were quite unkind."
★★★★★
2023-10-09
S

Stefan J

Couple
Main and Mountain ★★
"This is a good place. Very enjoyable stay here in June. Very practical and clean. Nicely appointed room. Modern approaches to keyless entry. Cozy coffee bar. Very pleasant."
★★★★★
2025-06-21
G

XX Guest User

Traveling with friends
The Pointe at Castle Hill Resort & Spa ★★★
"Everything was wonderful at The Pointe. However, the coffee that they put out in the morning is really just colored water, it is not edible, even if you are an addict. I've noticed more and more hotels are advertising coffee but then not making it correctly. I don't know if they are consciously trying to save money or if their front line employees prefer to use the previous day's grounds because it is somehow easier."
★★★★★
2026-02-07
M

US Mr. SQ

Family
Hampton Inn White River Junction ★★
"The hotel is pretty clean. The room is little bit smaller than expected. The breakfast is refilled quickly but the selection is limited. Overall I would recommend to others."
★★★★★
2026-01-05
G

Guest User

Family
On the River Inn ★★★★
"I have driven by this hotel many times.  Outside is uninspiring but the inside is beautiful.  Rooms very comfortable.  Lovely to have a deck to sit on.  We had a very nice stay. Recommend."
★★★★★
2026-07-29
G

Guest User

Traveling with friends
Best Western Springfield Hotel ★★★
"It's good. Each bed in the twin room is 1.5 meters, very large and clean. The bathroom is a little small but ok. The breakfast is very simple, but you can make your own waffles."
★★★★★
2024-10-08
_

_fengsuixindong_

Family
Hotel Coolidge ★★★
"A century-old store, you can personally feel the centuries-old vicissitudes of the building. The price is the cheapest nearby. If you want to experience the country style, you can try it. If you are used to staying in domestic luxury hotels, it is not recommended to come here. I saw the bearded man at the front desk saying enthusiastically to every guest who checked in: Oh, a very good discount price."
★★★★★
2023-10-11
A

CN Anonymous User

Family
Comfort Inn ★★
"Generally speaking, the hygiene is average, and there is always a musty smell in the room."
★★★★★
2024-09-09

Windsor County Travel Information

⚡

Power Plug & Voltage

120V/Type A/B

💵

Exchange Rate

1 AUD ≈ 0.70 USD

💳

Local Payment

Cards/ApplePay/Cash

📱

Connectivity

Verizon/AT&T/T-Mobile

🌡️

Current Weather

Cloudy with showers

More Information About Windsor County Hotels

Data

Detail

Number of reviews

3,409

Total properties

165

Weekday Avg. Price

AU$ 524

Weekend Avg. Price

AU$ 598

Trending hotel

Align Inn Vermont

FAQs About Hotels in Windsor County

Disclaimer: This article has been provided by an individual contributor or third party platform. If there is any discrepancy regarding the copyright, please contact us directly and we will delete the content immediately.