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
  • Includes a pool: The pool area is open from 5am until 11pm. It is an indoor, heated pool measuring 20' by 50'.
  • Mid-scale Highway property
More Photos Pool image of Best Western Springfield Hotel
From$106
Very Good 4.0 /5 Latest Reviews Call BookMore Details
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Pointe at Castle Hill Resort in Proctorsville 2940 State Route 103, Proctorsville, VT 05153
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~8.75 miles north of Chester
  • Has a pool!
  • Mid-scale Rural property
More Photos Swimming pool at Pointe at Castle Hill Resort
From$85
Very Good 4.0 /5 Read Reviews Call BookMore Details
Aspen at Manchester : 5669 Main St. 5669 Main St., Manchester, VT 05255
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~23.30 miles west of Chester
  • Includes a pool: Seasonal outdoor pool, generally open May - October.
  • 3 star Rural hotel
More Photos Pool image of Aspen at Manchester
From$80
Average 3.0 /5 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)
  • Affordable Resort hotel
More Photos Swimming pool at Palmer House Resort Ascend Hotel Collection
From$100
Average 3.0 /5 Latest 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 Pool image of On The River Inn Woodstock
From$125
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
  • Has swimming pool: Heated Outdoor Pool: Open seasonally from late-May to mid-October, from 9:00 a.m. to 9:00 p.m.
  • Cheap Mountain hotel
More Photos Swimming pool at Hideaway Inn Mt. Snow
From$50
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn Brattleboro 1378 Putney Rd., Brattleboro, VT 05301
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~25.68 miles south of Chester
  • Pool available: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • 3 star Rural hotel
More Photos Pool image of Hampton Inn Brattleboro
From$105
Very Good 4.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 in Brattleboro 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
  • Low Cost Highway property
More Photos Swimming pool at Comfort Inn & Suites Brattleboro I 91
From$79
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro 100 Chickering Dr., Brattleboro, VT 05301
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~26.53 miles south of Chester
  • Pool details: Indoor pool/ open 5am-11pm
  • Three Star Suburban property
More Photos Photo of Holiday Inn Express & Suites Brattleboro Pool
From$79
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Colonial Motel And Spa in Brattleboro 889 Putney Rd., Brattleboro, VT 05301
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~26.57 miles south of Chester
  • Pool available: INDOOR POOL: Monday-saturday 6am to 9pm Sunday : 8am to 9pm Holiday hours may vary It is 75feet Salt water pool with sauna,hot tub, limited gym equipment and locker room. OUTDOOR POOL: Seasonal. Open till dark.Not heated
  • 3 star Rural property
More Photos Pool image of Colonial Motel And Spa
From$59
Average 3.0 /5 Reviews Call BookMore Details
Hideaway Inn Mt. Sunapee 1403 New Hampshire Rte 103, Newbury, NH 03255
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~27.16 miles east of Chester
  • Pool in hotel
  • Mid-scale Resort property
More Photos Photo of Hideaway Inn Mt. Sunapee Pool
From$80
Average 3.0 /5 Review Score Call BookMore Details
Killington Mountain Lodge Tapestry Collection by Hilton in Killington 2617 Killington Rd., Killington, VT 05751
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~27.51 miles north of Chester
  • Pool details: We have a 25 person outdoor hot tub with a fire pit. Indoor pool.
  • 3-star Resort hotel
More Photos Swimming pool at Killington Mountain Lodge Tapestry Collection by Hilton
From$70
Average 3.0 /5 Reviews Call BookMore Details
Keene Elm City Hotel, an Ascend Collection Hotel 175 Key Rd., Keene, NH 03431
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~27.74 miles southeast of Chester
  • Includes a pool: Heated Indoor Pool Open from 6:30am-10:00pm
  • Two-star Rural hotel
More Photos Swimming pool at Keene Elm City Hotel, an Ascend Collection Hotel
From$95
Very Good 4.0 /5 Review Score Call BookMore Details
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Best Western Plus Keene Hotel : 401 Winchester St. 401 Winchester St., Keene, NH 03431
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~28.03 miles southeast of Chester
  • Has swimming pool: Indoor Heated Pool
  • Cheap Suburban hotel
More Photos Photo of Best Western Plus Keene Hotel Pool
From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western West Lebanon- Hanover Hotel 45 Airport Rd., West Lebanon, NH 03784
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~28.97 miles northeast of Chester
  • Pool available: Outdoor Seasonal Pool Open 9AM - 9PM during May- Sep
  • 2 star Airport property
More Photos Pool image of Best Western West Lebanon- Hanover Hotel
From$85
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
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Cortina Inn in Rutland 476 Holiday Dr., Rutland, VT 05701
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~28.98 miles northwest of Chester
  • Includes a swimming pool
  • Three Star Suburban property
More Photos Swimming pool at Cortina Inn
From$79
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn White River Junction 104 Ballardvale Dr., White River Junction, VT 05001
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~29.26 miles northeast of Chester
  • Includes a swimming pool
  • Midscale Downtown hotel
More Photos Swimming pool at Hampton Inn White River Junction
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301
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~29.34 miles south of Chester
  • We have a pool
  • Inexpensive Downtown hotel
More Photos Photo of Econo Lodge Brattleboro South Pool
From$53
Not Good 1.0 /5 Reviews Call BookMore Details
Comfort Inn Rutland Vt 19 Allen St., Rutland, VT 05701
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~29.65 miles northwest of Chester
  • Pool details: INDOOR HEATED POOL AND HOT TUB AREA OPEN 9 AM - 9:30 PM.
  • 2-star Downtown property
More Photos Photo of Comfort Inn Rutland Vt Pool
From$59
Very Good 4.0 /5 Read Reviews Call BookMore Details
The White House Inn - Wilmington 178 Vt 9 East, Wilmington, VT 05363
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~30.44 miles southwest of Chester
  • Pool available: Small, shallow indoor pool, open 24 hours a day
  • 4-star Mountain property
More Photos Photo of The White House Inn Pool
From$75
Average 3.0 /5 Read Reviews Call BookMore Details
Best Western Inn & Suites Rutland-Killington 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$80
Very Good 4.5 /5 Review Score 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 Swimming pool at Hilton Garden Inn Hanover Lebanon
From$129
Very Good 4.5 /5 Recent Reviews Call BookMore Details
The Mountain Top Inn & Resort 195 Mountain Top Rd., Chittenden, VT 05737
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~36.49 miles northwest of Chester
  • Has swimming pool
  • 4-star hotel
More Photos Pool image of The Mountain Top Inn & Resort
From$160
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Bennington 220 Northside Dr., Bennington, VT 05201
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~39.87 miles southwest of Chester
  • Includes a pool: Outdoor, seasonal
  • Economical Suburban hotel
More Photos Pool image of Best Western Bennington
From$36
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn Bennington 51 Hannaford Sq., Bennington, VT 05201
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~39.94 miles southwest of Chester
  • Includes a pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Affordable Mountain hotel
More Photos Photo of Hampton Inn Bennington Pool
From$80
Average 3.0 /5 Review Score Call BookMore Details
Henniker Motel 61 Craney Pond Rd., Henniker, NH 03242
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~40.87 miles east of Chester
  • Pool details: Heated indoor pool 8 AM - 10:00 PM
  • Inexpensive Mountain property
More Photos Swimming pool at Henniker Motel
From$90
Average 3.0 /5 Read Reviews Call BookMore Details

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