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.

Chester Hotels with Outdoor or Indoor Pools

Best Western Springfield Hotel 818 Charlestown Rd., Springfield, VT 05156 Call ~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'.
  • Midscale Highway property
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From$106
Very Good 4.0 /5 Review Score Call BookMore Details
Pointe at Castle Hill Resort 2940 State Route 103, Proctorsville, VT 05153 Call ~8.75 miles north of Chester
  • We have a pool
  • Affordable Rural property
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From$85
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Aspen at Manchester : 5669 Main St. 5669 Main St., Manchester, VT 05255 Call ~23.30 miles west of Chester
  • Includes a pool: Seasonal outdoor pool, generally open May - October.
  • Mid-scale Rural property
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Palmer House Resort Ascend Hotel Collection in Manchester Center 5383 Main St., Manchester Center, VT 05255 Call ~23.47 miles west of Chester
  • Has swimming pool: Indoor & Outdoor (seasonal)
  • 3 star Resort hotel
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From$100
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On The River Inn Woodstock - Woodstock 1653 West Woodstock Rd., Woodstock, VT 05091 Call ~24.03 miles north of Chester
  • Has swimming pool: Indoor Pool & Sauna – Relax and unwind, rain or shine. 7am - 10pm.
  • Four star Mountain hotel
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From$125
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Hideaway Inn Mt. Snow : 270 Handle Rd. 270 Handle Rd., Dover, VT 05356 Call ~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.
  • Two-star Mountain property
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From$50
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Hampton Inn Brattleboro 1378 Putney Rd., Brattleboro, VT 05301 Call ~25.68 miles south of Chester
  • Has swimming pool: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • 3 star Rural property
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From$105
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 : 1186 Putney Rd. 1186 Putney Rd., Brattleboro, VT 05301 Call ~26.00 miles south of Chester
  • Pool details: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Inexpensive Highway hotel
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From$79
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Holiday Inn Express & Suites Brattleboro 100 Chickering Dr., Brattleboro, VT 05301 Call ~26.53 miles south of Chester
  • Pool available: Indoor pool/ open 5am-11pm
  • Affordable Suburban hotel
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From$79
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Colonial Motel And Spa 889 Putney Rd., Brattleboro, VT 05301 Call ~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
  • Three Star Rural property
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From$59
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Hideaway Inn Mt. Sunapee 1403 New Hampshire Rte 103, Newbury, NH 03255 Call ~27.16 miles east of Chester
  • With a pool!
  • 3 star Resort hotel
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From$80
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Killington Mountain Lodge Tapestry Collection by Hilton 2617 Killington Rd., Killington, VT 05751 Call ~27.51 miles north of Chester
  • Pool available: We have a 25 person outdoor hot tub with a fire pit. Indoor pool.
  • Three Star Resort hotel
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From$70
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Keene Elm City Hotel, an Ascend Collection Hotel - Keene 175 Key Rd., Keene, NH 03431 Call ~27.74 miles southeast of Chester
  • Has swimming pool: Heated Indoor Pool Open from 6:30am-10:00pm
  • Two star Rural property
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From$95
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Best Western Plus Keene Hotel : 401 Winchester St. 401 Winchester St., Keene, NH 03431 Call ~28.03 miles southeast of Chester
  • Includes a pool: Indoor Heated Pool
  • Inexpensive Suburban property
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From$75
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Best Western West Lebanon- Hanover Hotel - West Lebanon 45 Airport Rd., West Lebanon, NH 03784 Call ~28.97 miles northeast of Chester
  • Includes a pool: Outdoor Seasonal Pool Open 9AM - 9PM during May- Sep
  • Cheap Airport hotel
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From$85
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Cortina Inn 476 Holiday Dr., Rutland, VT 05701 Call ~28.98 miles northwest of Chester
  • With a pool!
  • Affordable Suburban hotel
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From$79
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Hampton Inn White River Junction in White River Junction 104 Ballardvale Dr., White River Junction, VT 05001 Call ~29.26 miles northeast of Chester
  • Includes a swimming pool
  • Mid-scale Downtown hotel
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From$89
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Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301 Call ~29.34 miles south of Chester
  • With a pool!
  • 2-star Downtown hotel
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From$53
Not Good 1.0 /5 Recent Reviews Call BookMore Details
Comfort Inn Rutland Vt 19 Allen St., Rutland, VT 05701 Call ~29.65 miles northwest of Chester
  • Pool details: INDOOR HEATED POOL AND HOT TUB AREA OPEN 9 AM - 9:30 PM.
  • Cheap Downtown hotel
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From$59
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The White House Inn 178 Vt 9 East, Wilmington, VT 05363 Call ~30.44 miles southwest of Chester
  • Includes a pool: Small, shallow indoor pool, open 24 hours a day
  • High end Mountain hotel
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From$75
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Best Western Inn & Suites Rutland-Killington - Rutland 5 Best Western Place, Rutland, VT 05701 Call ~30.89 miles northwest of Chester
  • Includes a pool: Outdoor, heated salt water pool open seasonally*Closed for the 2025 season
  • 3-star Rural hotel
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From$80
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Hilton Garden Inn Hanover Lebanon 35 Labombard Rd., Lebanon, NH 03766 Call ~32.19 miles northeast of Chester
  • Pool details: Indoor salt water pool, ADA accessible - open 8am-11pm
  • 3 star Suburban hotel
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From$129
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The Mountain Top Inn & Resort 195 Mountain Top Rd., Chittenden, VT 05737 Call ~36.49 miles northwest of Chester
  • Includes a pool
  • 4-star property
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From$160
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Best Western Bennington - Bennington 220 Northside Dr., Bennington, VT 05201 Call ~39.87 miles southwest of Chester
  • Pool details: Outdoor, seasonal
  • 2 star Suburban property
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From$36
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Hampton Inn Bennington - Bennington 51 Hannaford Sq., Bennington, VT 05201 Call ~39.94 miles southwest of Chester
  • Pool available: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Three Star Mountain hotel
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From$80
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Henniker Motel 61 Craney Pond Rd., Henniker, NH 03242 Call ~40.87 miles east of Chester
  • Has swimming pool: Heated indoor pool 8 AM - 10:00 PM
  • Inexpensive Mountain hotel
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From$90
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