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
  • Pool in hotel: The pool area is open from 5am until 11pm. It is an indoor, heated pool measuring 20' by 50'.
  • 3-star Highway property
More Photos
From$106
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Club Vacations Ascutney Mountain Resort - Brownsville 485 Hotel Rd., Brownsville, VT 05037 Call ~15.23 miles northeast of Chester
  • Pool in hotel: Indoor Pool Outdoor Pool - Opened seasonally
  • Three Star Mountain hotel
More Photos
From$120
Very good 4.0 /5 Latest Reviews Call BookMore Details
Aspen at Manchester 5669 Main St., Manchester, VT 05255 Call ~23.30 miles west of Chester
  • Pool available: Seasonal outdoor pool, generally open May - October.
  • Mid-scale Rural hotel
More Photos
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Palmer House Resort Ascend Hotel Collection - Manchester Center 5383 Main St., Manchester Center, VT 05255 Call ~23.47 miles west of Chester
  • Pool available: Indoor & Outdoor (seasonal)
  • 3 star Resort property
More Photos
From$100
Average 3.0 /5 Latest Reviews Call BookMore Details
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.
  • High-end Mountain property
More Photos
From$125
Average 3.0 /5 Reviews Call BookMore Details
Hideaway Inn Mt. Snow - Dover 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.
  • Low-priced Mountain hotel
More Photos
From$50
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn Brattleboro in 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'
  • Affordable Rural hotel
More Photos
From$105
Very good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 in Brattleboro 1186 Putney Rd., Brattleboro, VT 05301 Call ~26.00 miles south of Chester
  • Pool available: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Low Cost Highway property
More Photos
From$79
Very good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express & Suites Brattleboro - Brattleboro 100 Chickering Dr., Brattleboro, VT 05301 Call ~26.53 miles south of Chester
  • Pool available: Indoor pool/ open 5am-11pm
  • Mid-scale Suburban hotel
More Photos
From$79
Very good 4.0 /5 Latest Reviews Call BookMore Details
Colonial Motel And Spa 889 Putney Rd., Brattleboro, VT 05301 Call ~26.57 miles south of Chester
  • Pool in hotel: 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
  • Affordable Rural property
More Photos
From$59
Average 3.0 /5 Latest Reviews Call BookMore Details
Hideaway Inn Mt. Sunapee : 1403 New Hampshire Rte 103 1403 New Hampshire Rte 103, Newbury, NH 03255 Call ~27.16 miles east of Chester
  • Has a pool!
  • Three Star Resort property
More Photos
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
The Mountain Inn at Killington 47 Old Mill Rd., Killington, VT 05751 Call ~27.31 miles northwest of Chester
  • Includes a pool
  • Midscale Resort property
More Photos
From$52
Very good 4.0 /5 Reviews Call BookMore Details
Courtyard by Marriott Keene Downtown in Keene 75 Railroad St., Keene, NH 03431 Call ~27.94 miles southeast of Chester
  • Pool details: Heated indoor pool
  • Three Star Downtown hotel
More Photos
From$99
Very good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Plus Keene Hotel in Keene 401 Winchester St., Keene, NH 03431 Call ~28.03 miles southeast of Chester
  • Has swimming pool: Indoor Heated Pool
  • Cheap Suburban property
More Photos
From$75
Very good 4.0 /5 Read Reviews Call BookMore Details
Best Western West Lebanon- Hanover Hotel in West Lebanon 45 Airport Rd., West Lebanon, NH 03784 Call ~28.97 miles northeast of Chester
  • Pool available: Outdoor Seasonal Pool Open 9AM - 9PM during May- Sep
  • 2 star Airport hotel
More Photos
From$85
Very good 4.0 /5 Latest Reviews Call BookMore Details
Cortina Inn 476 Holiday Dr., Rutland, VT 05701 Call ~28.98 miles northwest of Chester
  • With a pool!
  • Mid-scale Suburban hotel
More Photos
From$79
Average 3.0 /5 Read Reviews Call BookMore Details
The White River Inn & Suites : 91 Ballardvale Dr. 91 Ballardvale Dr., White River Junction, VT 05001 Call ~29.23 miles northeast of Chester
  • Has a pool!
  • Low-priced Highway hotel
More Photos
From$75
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn White River Junction 104 Ballardvale Dr., White River Junction, VT 05001 Call ~29.26 miles northeast of Chester
  • Pool in hotel
  • 3-star Downtown property
More Photos
From$89
Very good 4.0 /5 Guest Reviews Call BookMore Details
Econo Lodge Brattleboro South 515 Canal St., Brattleboro, VT 05301 Call ~29.34 miles south of Chester
  • Has swimming pool
  • Cheap Downtown property
More Photos
From$53
Terrible 1.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn Rutland Vt in Rutland 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 hotel
More Photos
From$59
Very good 4.0 /5 Review Score Call BookMore Details
The White House Inn - Wilmington 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
  • High-end Mountain hotel
More Photos
From$75
Average 3.0 /5 Hotel Reviews Call BookMore Details
Best Western Inn & Suites Rutland-Killington 5 Best Western Place, Rutland, VT 05701 Call ~30.89 miles northwest of Chester
  • Pool details: Outdoor, heated salt water pool open seasonally*Closed for the 2025 season
  • Midscale Rural hotel
More Photos
From$80
Very good 4.5 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Hanover Lebanon - Lebanon 35 Labombard Rd., Lebanon, NH 03766 Call ~32.19 miles northeast of Chester
  • Includes a pool: Indoor salt water pool, ADA accessible - open 8am-11pm
  • Affordable Suburban property
More Photos
From$129
Very good 4.5 /5 Read Reviews Call BookMore Details
Best Western Bennington - Bennington 220 Northside Dr., Bennington, VT 05201 Call ~39.87 miles southwest of Chester
  • Pool available: Outdoor, seasonal
  • Two star Suburban property
More Photos
From$36
Very good 4.0 /5 Review Score Call BookMore Details
Hampton Inn Bennington in 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 hotel
More Photos
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hotel Vervana Trademark Collection by Wyndham : 141 Main St. 141 Main St., Bennington, VT 05201 Call ~40.46 miles southwest of Chester
  • Pool details: Outdoor pool.
  • Affordable property
More Photos
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Henniker Motel in Henniker 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
  • Two star Mountain property
More Photos
From$90
Average 3.0 /5 Latest Reviews Call BookMore Details
Back to Top