Find Hotels with a Pool in Chester, VT
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Check availability on Chester Hotels with a Pool
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Aug 31 - Sep 1Tomorrow
Sep 1 - Sep 2This weekend
Sep 4 - Sep 6Next weekend
Sep 11 - Sep 13Our top choices for Chester hotels with a pool
1. Historic 150-year-old farmhouse, Jacuzzi included
Historic 150-year-old farmhouse, Jacuzzi includedChester Depot
- Historic farmhouse offers year-round aquatic enjoyment with well-maintained outdoor pool and hot tub.
$398 nightly
$445 total
Sep 8 - Sep 9
Total with taxes and fees
2. Pointe at Castle Hill Resort
Pointe at Castle Hill ResortCavendish
- Dive into alpine luxury with this heated indoor pool and hot tub sanctuary, steps away from Okemo Mountain's world-class skiing.
$100 nightly
$109 total
Sep 3 - Sep 4
Total with taxes and fees
3. The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic MountainLondonderry
- Slope-side sanctuary beckons with mountain vistas and a seasonal outdoor pool.
$82 nightly
$91 total
Oct 1 - Oct 2
Total with taxes and fees
4. Best Western Springfield Hotel
Best Western Springfield HotelSpringfield
- Splash into mountain views at this hotel's warm indoor pool, perfect for year-round aquatic bliss.
$179 nightly
$197 total
Sep 1 - Sep 2
Total with taxes and fees
5. Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic MountainLondonderry
- Swim in the sunlit mountain waters at this alpine retreat's seasonal outdoor pool nestled in picturesque Vermont.
$149 nightly
$164 total
Sep 1 - Sep 2
Total with taxes and fees
6. Jackson Gore Village, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts PropertyJackson Gore Base Area
- Dive into pool perfection at this mountain resort with year-round swimming and spa relaxation.
$179 nightly
$197 total
Sep 30 - Oct 1
Total with taxes and fees
$216 nightly
$235 total
Sep 7 - Sep 8
Total with taxes and fees
$179 nightly
$195 total
Sep 3 - Sep 4
Total with taxes and fees
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Top Chester Hotel Reviews
Colonial Motel
10/10 Excellent
"Staff was very helpful. A little seating area under some trees was a beautiful place to relax while the sun was setting."
Hampton Inn and Suites Manchester
10/10 Excellent
"WOW! Nicest Hampton Inn ever! The manager Stacy is over the top cordial, professional and helpful. I highly recommend this stay. Nice breakfast and all of the employees are doing a great job. Fun shopping nearby and great restaurant selections too. I would not hesitate to book a stay here again in the future."
Hampton Inn Brattleboro
10/10 Excellent
"Clean room and welcoming staff. Breakfast was well displayed."
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
10/10 Excellent
"There was a lot to love about Holiday Inn Club Vacations Mount Ascutney, especially for a larger family or group. Our three-bedroom villa was BY FAR the largest accommodation of our trip and surprisingly affordable. We had tons of room to spread out, a decent-sized kitchen for cooking, and FREE laundry—a huge win during a long road trip! The villa kitchen was helpful but pretty minimally stocked. Cooking utensils and cutting boards were lacking, so bring some basics if you plan to cook. Grills are available, but you’ll need charcoal. I’d recommend buying it and any groceries before arriving because the onsite marketplace is expensive. The biggest disappointment was the pool, which is closed through 2027. Traveling with kids, that was a major bummer and definitely something families should know before booking. The location is incredibly beautiful, tucked away on a Vermont mountainside, but it is truly in the middle of nowhere. Come prepared! Overall, the incredible amount of space and affordability made it work really well for our group. It wasn’t our favorite stay of the trip, but the value for a three-bedroom villa was hard to beat."
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
"Room was clean and staff was excellent. Breakfast was good and plentiful."
The Palmer House Resort, an Ascend Collection Hotel
10/10 Excellent
"Nice room and property. With was down."
The Equinox Golf Resort And Spa
10/10 Excellent
"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."
On The River Inn
10/10 Excellent
"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."
Best Western Plus Keene Hotel
8/10 Good
"Clean room breakfast was good"
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