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