Best Hotels in Windsor County

Explore Windsor County with 177 hotels near iconic landmarks, popular shopping streets, and top dining spots.

The Pointe at Castle Hill Resort & Spa
8.6 (103 reviews)

The Pointe at Castle Hill Resort & Spa ★★★

📍 2940 Route 103, Cavendish

"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."

Main and Mountain
9.3 (42 reviews)

Main and Mountain ★★

📍 112 Main Street, Ludlow

"Stayed here with our two kids for one night while looking at real estate in the area. Nicely updated and modern room. Email sent with check in codes for door made virtual check in a breeze. Excellent location. Able to walk to dinner and breakfast. Nice bath products as well. Highly recommend."

The Shire Woodstock
8.8 (100 reviews)

The Shire Woodstock ★★★

📍 46 Pleasant St, Woodstock

Jackson Gore Village on Okemo Mountain
8.5 (100 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."

Castle Hill Resort and Spa
8.8 (43 reviews)

Castle Hill Resort and Spa ★★★

📍 171 Castle Hill Dr, Cavendish

"We had a small wedding at the Castle. The location was beautiful and very private. Lisa Cormier was an amazing wedding coordinator. She accommodated our group which included babies, toddlers, pre-teens, teens, and my 95 year old grandmother. She was very responsive and made everything perfect. I couldn’t have done it without her. Fonze, the chef, provided one of the best meals I’ve ever had. We will definitely be back for dinner. Even with the menu being fine dining, the portions are very generous and all of our guests loved it. Our waitstaff, Kelly and her counterpart (didn’t catch her name) were also amazing! They provided everything we needed with quick service. They were so kind and patient, especially with all the kids being there. The hotel manager, Andy, is very welcoming and accommodating. The rooms are very clean and provided everything we needed and we were asked if we needed anything extra. The hotel has beautiful grounds and is well maintained. Beautiful scenery for all the photos! 10/10 would recommend."

Best Western Springfield Hotel
8.7 (101 reviews)

Best Western Springfield Hotel ★★★

📍 818 Charlestown Rd, Springfield

"Ski essential Twin room suitable for a family"

The Jackson
9.6 (100 reviews)

The Jackson ★★★★

📍 43 Senior Lane, Woodstock

Super 8 by Wyndham White River Junction
5.9 (109 reviews)

Super 8 by Wyndham White River Junction ★★

📍 442 N Hartland Rd, White River Junction

"Clean, close to attractions, and with plenty of restaurants nearby."

White River Inn & Suites
6.9 (106 reviews)

White River Inn & Suites ★★

📍 91 Ballardvale Dr, White River Junction

"The hotel is quite old, and many facilities need updating, especially the carpets in public areas and elevators, which are very worn."

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Guest Reviews for Windsor County Hotels

8.5
Excellent Traveler Rating
Real & verified guest reviews from around the world
G

CN Guest User

Traveling with friends
The Pointe at Castle Hill Resort & Spa ★★★
"Suitable for skiing, very close to Okemo. Facilities: Basic, just enough for a bed. Environment: Not many restaurants nearby, so bring your own. The hotel is very expensive; a simple meal will cost over $50."
★★★★★
2025-11-29
S

Stefan J

Couple
Main and Mountain ★★
"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."
★★★★★
2026-07-06
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
G

Guest User

Other
Castle Hill Resort and Spa ★★★
"A dream wedding venue and experience supported by a remarkably professional, caring, and detail-oriented team. The spa was a fantastic experience. Wonderful staff interactions and amenities for us and our wedding guests to enjoy throughout the weekend. The Castle is perfectly situated to provide a private and intimate experience while just a short drive to shops and restaurants. We have visited the venue in every season and can attest that it is beautiful no matter the time of year. We look forward to returning to stay at Castle Hill Resort & Spa for many years to come."
★★★★★
2024-10-19
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
G

US Guest User

Solo traveler
Super 8 by Wyndham White River Junction ★★
"It is a nice place to stay and it is clean I don’t go to the free breakfast in the morning because I am usually at work before it starts"
★★★★★
2026-05-08
G

Guest User

Family
White River Inn & Suites ★★
"It was the worse hotel ever I experienced"
★★★★☆
2026-05-16
_

_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
G

Guest User

Other
The Inn at Weathersfield ★★★★
"We were looking for a place in Southern Vermont to chill for a while. I googled and found this hideaway gem. At first when we arrived we were a little early and were told to come back at 3pm. No problem, rules are rules. We came back and were greeted by Peter Ivanov who gave us the background of The Inn at Weathersfield. We were shown to our room on the second floor, a little more history and cookies 🍪 for a treat. We had dinner reservations for 6:30 and were told they would be very busy on this Friday evening. Again we went to the dining area and continued to the bar, were Peter was now the bartender. We were amazed at his skills and knowledge of mixology as we waited to be seated. We were seated by Ivan Ivanov, Peter's brother and co-owner. The choices on the menu were wonderful and visually appealing as well as very delicious 😋. Our meals and conversations with Ivan and Peter and others on the staff were outstanding 👏. Well done. As we found the Inn by chance, we highly recommend it and hope others find it as enjoyable as we did. BTW, the restaurant was very busy that Friday night and must have quite a reputation by the locals and well as travelers like us. Enjoy, we did. Thank you Peter and Ivan for your hospitality."
★★★★★
2026-05-20

Windsor County Travel Information

⚡

Power Plug & Voltage

120V/Type A/B

💵

Exchange Rate

1 GBP ≈ 1.34 USD

💳

Local Payment

Cards/ApplePay/Cash

📱

Connectivity

Verizon/AT&T/T-Mobile

🌡️

Current Weather

Cloudy

More Information About Windsor County Hotels

Key Info

Details

Number of reviews

3,360

Total properties

177

Weekday Avg. Price

£240

Weekend Avg. Price

£271

Trending hotel

Align Inn Vermont

FAQ – Hotels in Windsor County

  • What is the average price of a hotel in Windsor County this weekend?

    According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Windsor County this weekend is £232 per night. For a 4-star hotel, the average cost is £525 per night. If you're looking for a luxury experience, 5-star hotels in Windsor County this weekend typically cost £744 per night.

  • How much do hotels in Windsor County cost per night on weekdays?

    Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Windsor County during weekdays is £205 per night. For a 4-star hotel, you can expect to pay around £465 per night. If you're seeking a luxury stay, 5-star hotels in Windsor County generally cost £617 per night on weekdays.

  • What are the best places to stay in Windsor County?

    Some of the best places to stay in Windsor County are near popular attractions like AT trailhead Woodstock VT, offering easy access to key sights and amenities.

  • What are some of the best hotels in Windsor County?

    The most popular Windsor County hotels for your stay: Align Inn Vermont (from £141), The Shire Woodstock (from £161) and On the River Inn (from £175) are the preferred hotels.

  • Which hotels in Windsor County are worth visiting for their spa experience?

    Feel tired from travelling? On the River Inn (from £175), Woodstock Inn & Resort (from £605) and The Pointe at Castle Hill Resort & Spa (from £106) provide highly rated spa services.

  • Which hotels in Windsor County have swimming pools?

    On the River Inn (from £175), Holiday Inn Club Vacations MOUNT ASCUTNEY RESORT by IHG (from £104) and White River Inn & Suites (from £102) are hotels with swimming pools. Stay at any of these hotels to enjoy a swimming pool!

  • What hotels in Windsor County offer an especially good breakfast ?

    Woodstock Inn & Resort (from £605),On the River Inn (from £175) and Holiday Inn Club Vacations MOUNT ASCUTNEY RESORT by IHG (from £104) provide high-quality breakfast. Start your day with a delicious breakfast!

  • How to get good deals on hotels in Windsor County?

    To get the best hotel deals, try these Trip.com tips: 1. Log In Trip.com first and unlock member-only rates and Trip Coins (loyalty points). 2. Book Midweek: Sun–Thurs stays are much cheaper than weekends. 3. Set Price Alerts: Monitor price drops and rebook if needed. 4. Use “We Price Match” Policy: If you find a lower price elsewhere, Trip.com will refund the difference. 5. Avoid major holidays, conventions, and big events. 6. Check the Deals Page to see what promotions are available now on Trip.com.

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