Chester Hotels with Pools - Outdoor/Indoor Pools in Chester VT

Chester hotels and motels with swimming pools that are perfect for a family are listed below. Search for cheap and discount hotel rates at hotels with a pool in or near Chester, VT for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Chester Vermont hotel and motel rooms for children. Review the list of Chester hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.

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Chester Hotels with Outdoor or Indoor Pools

Best Western Springfield Hotel : 818 Charlestown Rd. 818 Charlestown Rd., Springfield, VT 05156
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~8.01 miles east of Chester
  • Pool details: The pool area is open from 5am until 11pm. It is an indoor, heated pool measuring 20' by 50'.
  • Affordable Highway property
More Photos Photo of Best Western Springfield Hotel Pool
From$127 total
Very good 4.0 /5 Read Reviews Call BookMore Details
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Holiday Inn Club Vacations Ascutney Mountain Resort in Brownsville 485 Hotel Rd., Brownsville, VT 05037
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~15.23 miles northeast of Chester
  • Pool in hotel: Indoor Pool Outdoor Pool - Opened seasonally
  • 3-star Mountain property
More Photos Photo of Holiday Inn Club Vacations Ascutney Mountain Resort Pool
From$144 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Aspen at Manchester 5669 Main St., Manchester, VT 05255
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~23.30 miles west of Chester
  • Pool in hotel: Seasonal outdoor pool, generally open May - October.
  • Midscale Rural property
More Photos Pool image of Aspen at Manchester
From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Palmer House Resort Ascend Hotel Collection 5383 Main St., Manchester Center, VT 05255
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~23.47 miles west of Chester
  • Pool in hotel: Indoor & Outdoor (seasonal)
  • 3-star Resort property
More Photos Photo of Palmer House Resort Ascend Hotel Collection Pool
From$120 total
Average 3.0 /5 Recent Reviews Call BookMore Details
On The River Inn Woodstock 1653 West Woodstock Rd., Woodstock, VT 05091
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~24.03 miles north of Chester
  • Has swimming pool: Indoor Pool & Sauna – Relax and unwind, rain or shine. 7am - 10pm.
  • Four-star Mountain hotel
More Photos Swimming pool at On The River Inn Woodstock
From$150 total
Average 3.0 /5 Read Reviews Call BookMore Details
Hideaway Inn Mt. Snow 270 Handle Rd., Dover, VT 05356
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~25.50 miles southwest of Chester
  • Pool details: Heated Outdoor Pool: Open seasonally from late-May to mid-October, from 9:00 a.m. to 9:00 p.m.
  • Inexpensive Mountain property
More Photos Swimming pool at Hideaway Inn Mt. Snow
From$60 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Brattleboro - Brattleboro 1378 Putney Rd., Brattleboro, VT 05301
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~25.68 miles south of Chester
  • Includes a pool: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • 3-star Rural hotel
More Photos Swimming pool at Hampton Inn Brattleboro
From$126 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 : 1186 Putney Rd. 1186 Putney Rd., Brattleboro, VT 05301
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~26.00 miles south of Chester
  • Includes a pool: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Two-star Highway property
More Photos Photo of Comfort Inn & Suites Brattleboro I 91 Pool
From$94 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Black Mountain Inn : 959 Putney Rd. 959 Putney Rd., Brattleboro, VT 05301
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~26.48 miles south of Chester
  • Has swimming pool: Seasonal outdoor pool
  • Economy Suburban property
More Photos Swimming pool at Black Mountain Inn
From$68 total
Average 3.5 /5 Review Score Call BookMore Details
Holiday Inn Express & Suites Brattleboro 100 Chickering Dr., Brattleboro, VT 05301
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~26.53 miles south of Chester
  • Has swimming pool: Indoor pool/ open 5am-11pm
  • Three Star Suburban hotel
More Photos Pool image of Holiday Inn Express & Suites Brattleboro
From$94 total
Very good 4.0 /5 Read Reviews Call BookMore Details
Hideaway Inn Mt. Sunapee - Newbury 1403 New Hampshire Rte 103, Newbury, NH 03255
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~27.16 miles east of Chester
  • We have a pool
  • Mid-scale Resort hotel
More Photos Photo of Hideaway Inn Mt. Sunapee Pool
From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
The Mountain Inn at Killington - Killington 47 Old Mill Rd., Killington, VT 05751
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~27.31 miles northwest of Chester
  • Has swimming pool
  • Midscale Resort hotel
More Photos Pool image of The Mountain Inn at Killington
From$62 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
Keene Elm City Hotel - Keene 175 Key Rd., Keene, NH 03431
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~27.74 miles southeast of Chester
  • Has swimming pool: Heated Indoor Pool Open from 6:30am-10:00pm
  • 3 star Rural property
More Photos Pool image of Keene Elm City Hotel
From$96 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
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Courtyard by Marriott Keene Downtown : 75 Railroad St. 75 Railroad St., Keene, NH 03431
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~27.94 miles southeast of Chester
  • Pool details: Heated indoor pool
  • Three Star Downtown hotel
More Photos Pool image of Courtyard by Marriott Keene Downtown
From$118 total
Very good 4.0 /5 Review Score Call BookMore Details
Best Western Plus Keene Hotel - Keene 401 Winchester St., Keene, NH 03431
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~28.03 miles southeast of Chester
  • Pool in hotel: Indoor Heated Pool
  • Cheap Suburban property
More Photos Swimming pool at Best Western Plus Keene Hotel
From$90 total
Very good 4.0 /5 Guest Reviews Call BookMore Details
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Best Western West Lebanon- Hanover Hotel 45 Airport Rd., West Lebanon, NH 03784
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~28.97 miles northeast of Chester
  • Pool in hotel: Outdoor Seasonal Pool Open 9AM - 9PM during May- Sep
  • Economy Airport property
More Photos Swimming pool at Best Western West Lebanon- Hanover Hotel
From$102 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Cortina Inn - Rutland 476 Holiday Dr., Rutland, VT 05701
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~28.98 miles northwest of Chester
  • Has a pool!
  • 3 star Suburban hotel
More Photos Photo of Cortina Inn Pool
From$94 total
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn White River Junction : 104 Ballardvale Dr. 104 Ballardvale Dr., White River Junction, VT 05001
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~29.26 miles northeast of Chester
  • Pool in hotel
  • Affordable Downtown hotel
More Photos Photo of Hampton Inn White River Junction Pool
From$106 total
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301
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~29.34 miles south of Chester
  • With a pool!
  • 2 star Downtown property
More Photos Swimming pool at Econo Lodge Brattleboro South
From$63 total
Terrible 1.0 /5 Reviews Call BookMore Details
Comfort Inn Rutland Vt in Rutland 19 Allen St., Rutland, VT 05701
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~29.65 miles northwest of Chester
  • Pool in hotel: INDOOR HEATED POOL AND HOT TUB AREA OPEN 9 AM - 9:30 PM.
  • Cheap Downtown hotel
More Photos Photo of Comfort Inn Rutland Vt Pool
From$70 total
Very good 4.0 /5 Latest Reviews Call BookMore Details
The White House Inn in Wilmington 178 Vt 9 East, Wilmington, VT 05363
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~30.44 miles southwest of Chester
  • Has swimming pool: Small, shallow indoor pool, open 24 hours a day
  • 4 star Mountain hotel
More Photos Swimming pool at The White House Inn
From$90 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Best Western Inn & Suites Rutland-Killington in Rutland 5 Best Western Place, Rutland, VT 05701
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~30.89 miles northwest of Chester
  • Pool details: Outdoor, heated salt water pool open seasonally*Closed for the 2025 season
  • 3-star Rural hotel
More Photos Swimming pool at Best Western Inn & Suites Rutland-Killington
From$96 total
Very good 4.5 /5 Reviews Call BookMore Details
Hilton Garden Inn Hanover Lebanon 35 Labombard Rd., Lebanon, NH 03766
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~32.19 miles northeast of Chester
  • Pool details: Indoor salt water pool, ADA accessible - open 8am-11pm
  • 3 star Suburban hotel
More Photos Pool image of Hilton Garden Inn Hanover Lebanon
From$154 total
Very good 4.5 /5 Latest Reviews Call BookMore Details
Hampton Inn Bennington - Bennington 51 Hannaford Sq., Bennington, VT 05201
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~39.94 miles southwest of Chester
  • Has swimming pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Affordable Mountain property
More Photos Swimming pool at Hampton Inn Bennington
From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
Hotel Vervana Trademark Collection by Wyndham - Bennington 141 Main St., Bennington, VT 05201
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~40.46 miles southwest of Chester
  • Includes a pool: Outdoor pool.
  • Affordable hotel
More Photos hotel room
From$96 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Henniker Motel 61 Craney Pond Rd., Henniker, NH 03242
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~40.87 miles east of Chester
  • Pool available: Heated indoor pool 8 AM - 10:00 PM
  • Two-star Mountain property
More Photos Pool image of Henniker Motel
From$108 total
Average 3.0 /5 Hotel Reviews Call BookMore Details

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