Best Hotels in Windsor County

Explore Windsor County with 163 stays near popular landmarks, shopping malls, dining spots, and key business areas for a convenient city stay.

Jackson Gore Village on Okemo Mountain
8.6 (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."

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

"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 Hartness House
8.2 (71 reviews)

The Hartness House ★★★

📍 109 Front St, Springfield

Stone Hearth Inn and Eatery
9.1 (51 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 (103 reviews)

The Pointe at Castle Hill Resort & Spa ★★★

📍 2940 Route 103, Cavendish

"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."

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

Find Your Perfect Stay in Windsor County by Travel Style

Castle Hill Resort and Spa Hotels in Windsor County

Castle Hill Resort and Spa

"There’s truly no way to describe our experience other than an absolute dream. We feel unbelievably lucky to have found this hidden gem of a venue. Part of me wants to keep it a secret forever, but it’s far too special not to share! In late August 2025, we hosted our fairytale wedding weekend here with Lisa and her incredible team. The Castle itself is full of beautifully maintained natural charm, with stunning views and endless photo opportunities around every corner. We were searching for a place that captured the warmth and romance of a villa for our Italian heritage-filled celebration, and Lisa (along with Kelly) brought that vision to life so effortlessly. By the end of the weekend, Lisa truly felt like part of our family. The entire team is warm, supportive, and incredibly on top of everything. They really do CARE. And we were not an easy group. We had kids, dogs (which I do not recommend!), unique traditions, food allergies, and very high expectations when it came to the food. Not only did they handle every detail with ease, but the food far exceeded those expectations. Our guest list was full of self-proclaimed Tri-State food critics, and the filet was an absolute standout! Every dish was thoughtful, delicious, and perfectly executed, and every dietary need was accommodated seamlessly without ever compromising quality or flavor. Thank you, Chef Harris!! The tent was an incredible perk and gave us a beautiful blank slate to bring our vision to life. That said, for a smaller wedding, it can feel a bit large, and the dance floor is on the smaller side so that's something to keep in mind depending on your guest count and priorities. Like any venue, there are guidelines in place to protect the space and ensure everything runs smoothly. They are especially firm on the dinner timeline, which ultimately keeps the entire weekend flowing seamlessly, but it’s helpful to be aware of that upfront when planning. The entire weekend felt warm, seamless, and completely one-of-a-kind. We couldn’t have imagined a better experience."

The Weston Hotels in Windsor County

The Weston

See All Hotels in This Style

Real Reviews of Windsor County Hotels From Travellers

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 ★★
"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

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

CA Guest User

Couple
On the River Inn ★★★★
"love this place … decor pool pool room lounge childrens play room.  all delighters"
★★★★★
2025-12-14
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 PHP ≈ 0.02 USD

💳

Local Payment

Cards/ApplePay/Cash

📱

Connectivity

Verizon/AT&T/T-Mobile

🌡️

Current Weather

Mostly cloudy

More Information About Windsor County Hotels

Data

Detail

Number of reviews

3,356

Total properties

163

Weekday Avg. Price

PHP 22,790

Weekend Avg. Price

PHP 25,926

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.