A lake surrounded by autumn-colored trees and a rocky shoreline.

Hotels with Swimming Pool in Pittsfield, Vermont

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Check availability on Pittsfield Hotels with Swimming Pool

Tonight
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Pittsfield hotels with a pool

A pool area with a wooden building, outdoor seating, and umbrellas.
A spacious room with large windows, a stone wall, and a wooden ceiling.
A lodge with a fire pit, outdoor seating, and a covered area with string lights.
A spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.

1. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
  • Lakeside resort oasis offers pool lounging with mountain vistas, after thrilling ski adventures.
P15,747
P17,165 total
includes taxes & fees
Nov 1 - Nov 2
The Mountain Top Inn & Resort
A pool area with lounge chairs and umbrellas, surrounded by landscaped gardens and a building with large windows.
A stone fireplace with a fire, a log, and a person reading a book.
A rustic interior with a stone hot tub, wooden furniture, and a mountain mural.
An outdoor seating area with tables and chairs, a stone planter with flowers, and a building with a sloped roof and large windows.

2. Summit Lodge

Summit Lodge
Killington
  • Alpine relaxation awaits at Killington inn with 2 outdoor pools, hot tub, and poolside bar.
P10,714
P13,392 total
includes taxes & fees
Oct 16 - Oct 17
Summit Lodge
A multi-story building with a pool and a covered patio area.
A bar area with a star sign, bicycles, and a patterned carpet.
A bathroom with a large freestanding bathtub, a mirror, and a wooden vanity.
A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

3. North Star Lodge and Resort

North Star Lodge and Resort
Killington
  • Refreshing heated outdoor pool at Killington resort with sauna and fitness center complements ski adventures.
P8,684
P9,553 total
includes taxes & fees
Oct 20 - Oct 21
North Star Lodge and Resort
A swimming pool surrounded by snow, with a building in the background.
A modern bathroom with a large bathtub, a glass-enclosed shower, and a toilet.
A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.
A lobby with a stone wall, wooden staircase, and a reception desk.

4. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
  • Splash into alpine bliss at this mountain inn's heated outdoor pool with scenic resort views.
P8,421
P9,727 total
includes taxes & fees
Oct 19 - Oct 20
The Mountain Inn at Killington
A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.
A kitchen with wooden cabinets, a stainless steel refrigerator, a stove, and two bar stools.
A Best Western Inn & Suites with a well-maintained lawn, a parking area, and a building with a porch.
A modern hotel lobby with a dining area, stone wall, and a view of the outside.

5. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
Rutland
  • Outdoor pool oasis for summer stays near slopes, with year-round adventures waiting just outside your door.
P10,118
P11,129 total
includes taxes & fees
Oct 21 - Oct 22
Best Western Inn & Suites Rutland-Killington
A pool area with lounge chairs and a view of a mountainous landscape.
A restaurant interior with stone walls, wooden tables and booths, and pendant lighting.
A sign for the Grand Hotel Spa in Killington, Vermont, with a mountain backdrop.
A reception desk with a stone wall backdrop and wooden accents, a person with a suitcase, and a television screen above the desk.

6. Killington Grand Hotel

Killington Grand Hotel
Base Area
  • Ski slope to steamy soaks: heated outdoor pool and hot tubs deliver mountain views after your slope adventures.
P14,549
P17,066 total
includes taxes & fees
Oct 12 - Oct 13
Killington Grand Hotel
An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.
A brick building with a sign reading 'Southside Steakhouse' and the number '170' above the entrance.
A modern bathroom with a large mirror, dual sinks, a glass shower enclosure, and neatly folded towels on shelves.
A hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.

7. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
  • Soak in pure relaxation at this mountain getaway, where the indoor pool beckons after exhilarating ski adventures nearby.
P6,985
P7,683 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn Rutland - Killington
An indoor swimming pool with clear glass walls, a wooden ceiling, and a tiled floor.
A modern lounge area with orange upholstered chairs, a fireplace, and large windows offering a view of autumn trees.
A covered outdoor area with a wooden ceiling, potted plants, and a bench.
A hotel room with a bed, a TV, a fireplace, a desk, and a chair.

8. Hampton Inn Rutland

Hampton Inn Rutland
Rutland
  • Splash into family fun with an indoor pool sanctuary at this hotel where winter adventures meet waterside bliss.
P8,720
P9,592 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn Rutland
A large house with a swimming pool, a fenced yard, and a well-lit entrance.
A long corridor with tables and chairs, large windows, and a ceiling fan.
Front of property
A paved patio with outdoor furniture, a decorative garden bed, and a white fence.

9. Brandon Inn

Brandon Inn
Brandon
  • Dive into a refreshing outdoor pool retreat at this historic hotel with loungers for sun-soaked relaxation.
P8,449
P9,294 total
includes taxes & fees
Nov 1 - Nov 2
Brandon Inn
A large indoor swimming pool with clear blue tiles, sunlit by large windows, and equipped with lounge chairs and a ceiling fan.
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.
Two Adirondack chairs by a river with a forested hillside in the background.
A spacious living room with a large American flag, a fireplace, and a chandelier.

10. On The River Inn

On The River Inn
West Woodstock
  • Splash into bliss with an indoor pool, hot tub, and children's splash area amid scenic views.
P10,248
P12,654 total
includes taxes & fees
Nov 1 - Nov 2
On The River Inn
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The staff went out of way to help and accommodate us. The chef was great"
Shirlee 3-night trip
Posted 1 hour ago
The Mountain Inn at Killington
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Quiet, friendly staff"
Janine 1-night trip
Posted 3 hours ago
Days Inn by Wyndham Rutland/Killington Area
Greenbrier Inn

Greenbrier Inn

10/10 Excellent
"If you are looking for a rustic, vintage, COZY, stay, then this place is for you. It was very comfortable and the owners were very kind and helpful. We thoroughly enjoyed our stay."
Erin 2-night trip
Posted 5 hours ago
Greenbrier Inn
On The River Inn

On The River Inn

8/10 Good
"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."
Loxley 3-night trip
Posted 1 day ago
On The River Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Still love the pool and hot tub"
Paul 2-night trip
Posted 5 days ago
Comfort Inn Rutland - Killington
Killington Grand Hotel

Killington Grand Hotel

8/10 Good
"Outdated but well kept. Pool and hot tub are amazing."
Julian 1-night trip
Posted 5 days ago
Killington Grand Hotel

Frequently asked questions

What are some accommodations with pools in Pittsfield?
The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool, and free self parking. Woodstock Inn & Resort: Provides a seasonal outdoor pool, an indoor pool, and 4 restaurants. Killington Mountain Lodge, Tapestry Collection by Hilton: Features 8 hot tubs, a seasonal outdoor pool, and a sauna. The Jackson: Features a children's pool, an indoor pool, and a sauna. Emrose Luxury Cabins: Offers a snack bar/deli, a seasonal outdoor pool, and daily.
What is there to see and do in Pittsfield?
Surround yourself with nature at Green Mountain National Forest. Discover sights such as Pittsfield Town Hall and Roger Clark Memorial Central Library during your stay.
When is the best time to book a hotel with a pool in Pittsfield?
Taking into account the local weather in Pittsfield can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.

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