Proctorsville Hotel Guide - Hotels with Pool in Proctorsville, Cavendish

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Proctorsville Hotels with Pool

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Proctorsville hotels with a pool

Indoor pool
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (936)
"Great place to stay while skiing at okemo"
United States
Ken
The price is €164
includes taxes & fees
4 Jan - 5 Jan 2026
Pointe at Castle Hill Resort
Lobby lounge
Castle Hill Resort And Spa

Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (104)
"Convenient that there is a restaurant is in the Castle, we also loved the outdoor hot tub and pool. "
United States
Jeff
The price is €249
includes taxes & fees
6 Jan - 7 Jan 2026
Castle Hill Resort And Spa
Outdoor pool, a heated pool
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
The price is €469
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Indoor pool
Best Western Springfield Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (808)
"The staff were very friendly; the breakfast was awesome. the pool was heated just right, and the room was very clean, I will stay here again. Good job Best western,"
United States
Jose
The price is €142
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Springfield Hotel
Outdoor pool
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very good, (688)
"This place was a dream, everybody was so nice! We felt at home and safe."
United States
Gracie
The price is €105
includes taxes & fees
7 Jan - 8 Jan 2026
The Upper Pass Lodge at Magic Mountain
Indoor pool, seasonal outdoor pool
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (781)
"Clean room, very nice staff, everything was excellent! "
United States
Karen
The price is €133
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1002)
"Rearaurant staff was top notch. "
United States
Daniel
On The River Inn
Seasonal outdoor pool
Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113)
"Lovely pleasant stay. "
United States
Heather
The price is €167
includes taxes & fees
4 Jan - 5 Jan 2026
Blue Gentian Lodge at Magic Mountain
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is €335
includes taxes & fees
19 Jan - 20 Jan 2026
Woodstock Inn & Resort
Exterior
Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (10)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
United States
Amy S.
The price is €475
includes taxes & fees
8 Jan - 9 Jan 2026
Historic 150-year-old farmhouse, Jacuzzi included
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.
View all properties

Top Proctorsville Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"The Inn was quite nice. We enjoyed the 2nd floor library area to sit and relax. The restaurant on site 506 Bistro was fabulous. "
Roy 3-night trip
Posted 1 day ago
On The River Inn

Frequently asked questions

What are some hotels with pools in Proctorsville?
Pointe at Castle Hill Resort: Features a full-service spa, an indoor pool and free self parking. Castle Hill Resort And Spa: Offers an indoor pool, an outdoor pool and a full-service spa. Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing: Provides a sauna, a communal pool and 1 hot tub. Killington Mountain Lodge, Tapestry Collection by Hilton: Offers a seasonal outdoor pool, an indoor pool and 4 restaurants. Woodstock Inn & Resort: Hotel, 1-minute walk from Killington Resort. Features daily, an outdoor pool and free self parking.
What is there to see and do in Proctorsville?
Explore places such as Okemo Mountain Resort and Killington Resort while you're in the area. The picturesque settings of Lake Rescue and Buttermilk Falls showcase the area's natural beauty. The mountain views, skiing and restaurants are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Proctorsville?
Taking the local weather in Proctorsville into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Proctorsville are January, March, November and February, with each month seeing an average of 35 cm of snowfall.