Jamaica Hotels with Outdoor or Indoor Pools

Hideaway Inn Mt. Snow 270 Handle Rd., Dover, VT 05356 Call ~9.87 miles southwest of Jamaica
  • Pool details: Heated Outdoor Pool: Open seasonally from late-May to mid-October, from 9:00 a.m. to 9:00 p.m.
  • Low Cost Mountain property
From$50
Average 3.0 /5 Review Score Call BookMore Details
Palmer House Resort Ascend Hotel Collection in Manchester Center 5383 Main St., Manchester Center, VT 05255 Call ~15.06 miles west of Jamaica
  • Includes a pool: Indoor & Outdoor (seasonal)
  • Mid-scale Resort hotel
From$100
Average 3.0 /5 Reviews Call BookMore Details
Aspen at Manchester 5669 Main St., Manchester, VT 05255 Call ~15.10 miles west of Jamaica
  • Includes a pool: Seasonal outdoor pool, generally open May - October.
  • 3-star Rural hotel
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
The White House Inn in Wilmington 178 Vt 9 East, Wilmington, VT 05363 Call ~15.41 miles south of Jamaica
  • Has swimming pool: Small, shallow indoor pool, open 24 hours a day
  • High-end Mountain hotel
From$75
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Brattleboro - Brattleboro 1378 Putney Rd., Brattleboro, VT 05301 Call ~17.41 miles southeast of Jamaica
  • Pool details: Indoor heated salt water pool and whirl pool Tub. The pool is 4' - 5'deep 15'x30'
  • Midscale Rural hotel
From$105
Very Good 4.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites Brattleboro I 91 in Brattleboro 1186 Putney Rd., Brattleboro, VT 05301 Call ~17.58 miles southeast of Jamaica
  • Pool in hotel: open 6am-10pm indoor heated pool. 3 foot deep to 5 foot deep
  • Two-star Highway hotel
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 ~17.74 miles southeast of Jamaica
  • Pool available: Indoor pool/ open 5am-11pm
  • Mid-scale Suburban hotel
From$79
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Colonial Motel And Spa : 889 Putney Rd. 889 Putney Rd., Brattleboro, VT 05301 Call ~17.90 miles southeast of Jamaica
  • 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
  • Mid-scale Rural property
From$59
Average 3.0 /5 Recent Reviews Call BookMore Details
Econo Lodge Brattleboro South in Brattleboro 515 Canal St., Brattleboro, VT 05301 Call ~19.97 miles southeast of Jamaica
  • Includes a swimming pool
  • Cheap Downtown hotel
From$53
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Best Western Springfield Hotel - Springfield 818 Charlestown Rd., Springfield, VT 05156 Call ~21.55 miles northeast of Jamaica
  • Pool in hotel: The pool area is open from 5am until 11pm. It is an indoor, heated pool measuring 20' by 50'.
  • Affordable Highway hotel
From$106
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Pointe at Castle Hill Resort 2940 State Route 103, Proctorsville, VT 05153 Call ~21.94 miles north of Jamaica
  • Includes a pool
  • Mid-scale Rural property
From$85
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Bennington - Bennington 220 Northside Dr., Bennington, VT 05201 Call ~25.04 miles southwest of Jamaica
  • Has swimming pool: Outdoor, seasonal
  • Inexpensive Suburban property
From$36
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Hampton Inn Bennington 51 Hannaford Sq., Bennington, VT 05201 Call ~25.25 miles west of Jamaica
  • Has swimming pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
  • Affordable Mountain property
From$80
Average 3.0 /5 Reviews Call BookMore Details
Keene Elm City Hotel, an Ascend Collection Hotel : 175 Key Rd. 175 Key Rd., Keene, NH 03431 Call ~26.72 miles east of Jamaica
  • Has swimming pool: Heated Indoor Pool Open from 6:30am-10:00pm
  • Low priced Rural property
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Plus Keene Hotel in Keene 401 Winchester St., Keene, NH 03431 Call ~26.96 miles east of Jamaica
  • Includes a pool: Indoor Heated Pool
  • Inexpensive Suburban hotel
From$75
Very Good 4.0 /5 Review Score Call BookMore Details
The Porches Inn at Mass Moca : 231 River St. 231 River St., North Adams, MA 01247 Call ~31.03 miles southwest of Jamaica
  • Includes a pool: Outdoor heated pool open 24 hours daily year round. Sauna, outdoor hot tub and 24 hour fitness Center onsite.
  • High end Downtown property
From$199
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hotel Downstreet Ascend Hotel Collection 40 Main St., North Adams, MA 01247 Call ~31.25 miles southwest of Jamaica
  • Pool in hotel: 5am-10pm Indoor
  • Midscale Downtown hotel
From$136
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Maple Terrace Motel - Williamstown 555 Main St., Williamstown, MA 01267 Call ~33.10 miles southwest of Jamaica
  • Pool available: Beautiful secluded heated pool with amazing and breathtaking views. Opens Daily 9 AM and closes at Dusk.
  • Low priced Rural property
From$59
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Cortina Inn 476 Holiday Dr., Rutland, VT 05701 Call ~35.91 miles north of Jamaica
  • We have a pool
  • 3 star Suburban property
From$79
Average 3.0 /5 Latest Reviews Call BookMore Details
Comfort Inn Rutland Vt 19 Allen St., Rutland, VT 05701 Call ~36.79 miles north of Jamaica
  • Includes a pool: INDOOR HEATED POOL AND HOT TUB AREA OPEN 9 AM - 9:30 PM.
  • Economical Downtown property
From$59
Very Good 4.0 /5 Reviews Call BookMore Details
On The River Inn Woodstock in Woodstock 1653 West Woodstock Rd., Woodstock, VT 05091 Call ~38.26 miles north of Jamaica
  • Pool in hotel: Indoor Pool & Sauna – Relax and unwind, rain or shine. 7am - 10pm.
  • 4 star Mountain hotel
From$125
Average 3.0 /5 Review Score Call BookMore Details
Killington Mountain Lodge Tapestry Collection by Hilton 2617 Killington Rd., Killington, VT 05751 Call ~38.29 miles north of Jamaica
  • Pool available: We have a 25 person outdoor hot tub with a fire pit. Indoor pool.
  • Three Star Resort hotel
From$70
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Inn & Suites Rutland-Killington - Rutland 5 Best Western Place, Rutland, VT 05701 Call ~39.05 miles north of Jamaica
  • Has swimming pool: Outdoor, heated salt water pool open seasonally*Closed for the 2025 season
  • Midscale Rural property
From$80
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Hideaway Inn Mt. Sunapee - Newbury 1403 New Hampshire Rte 103, Newbury, NH 03255 Call ~40.23 miles east of Jamaica
  • Includes a swimming pool
  • Three Star Resort property
From$80
Average 3.0 /5 Review Score Call BookMore Details
Vacation Village in The Berkshires 276 Brodie Mtn Rd., Lanesborough, MA 01237 Call ~43.00 miles southwest of Jamaica
  • Pool in hotel: Pool hours 8am - 11pm Vacation Village in the Berkshires has a heated indoor swimming pool inside the clubhouse and a heated outdoor swimming pool located behind the clubhouse. Weather permitting, the outdoor pool is open seasonally from Memorial Day through Labor Day. Poolside lounge chairs are available to our owners and guests on a first-come, first-served basis. Pool towels are provided at each pool.
  • Midscale Mountain property
From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Jiminy Peak Mountain Resort : 37 Corey Rd. 37 Corey Rd., Hancock, MA 01237 Call ~44.40 miles southwest of Jamaica
  • Includes a pool: Country Inn Pool is open 8a - 10p daily. Outdoor heated pool open year round.
  • Affordable Mountain hotel
From$105
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western West Lebanon- Hanover Hotel 45 Airport Rd., West Lebanon, NH 03784 Call ~44.52 miles northeast of Jamaica
  • Pool available: Outdoor Seasonal Pool Open 9AM - 9PM during May- Sep
  • Inexpensive Airport hotel
From$85
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn White River Junction 104 Ballardvale Dr., White River Junction, VT 05001 Call ~44.72 miles northeast of Jamaica
  • We have a pool ready for use
  • Three Star Downtown property
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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