Chesterfield Hotels with Outdoor or Indoor Pools
Mountaineer Inn - Dover
+1-888-788-5576
270 Handle Rd., Dover, VT 05356
+1-888-788-5576
~20.16 miles west of Chesterfield
- 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 property
Best Western Springfield Hotel
+1-888-311-4278
818 Charlestown Rd., Springfield, VT 05156
+1-888-311-4278
~26.05 miles north of Chesterfield
- Includes a pool: The pool area is open from 5am until 11pm. It is an indoor, heated pool measuring 20'' by 50''.
- 3 star Highway property
The Porches Inn at Mass Moca in North Adams
+1-888-469-4795
231 River St., North Adams, MA 01247
+1-888-469-4795
~33.59 miles west of Chesterfield
- Has swimming pool: Outdoor heated pool open 24 hours daily year round. Sauna, outdoor hot tub and 24 hour fitness Center onsite.
- Expensive Downtown property
Aspen at Manchester
+1-888-455-5160
5669 Main St., Manchester, VT 05255
+1-888-455-5160
~34.06 miles northwest of Chesterfield
- Pool available: Seasonal outdoor pool, generally open May - October.
- Mid-scale Rural hotel
Colonial Hotel - Gardner
+1-888-749-6785
625 Betty Spring Rd., Gardner, MA 01440
+1-888-749-6785
~35.90 miles southeast of Chesterfield
- Has swimming pool: Pool Hours 5am-10pm
- Affordable Mountain hotel
Hampton Inn Bennington
+1-888-878-9982
51 Hannaford Sq., Bennington, VT 05201
+1-888-878-9982
~36.44 miles west of Chesterfield
- Includes a pool: Indoor Pool is open from 7AM-10PM daily. Pool is 12,000 gallons
- Affordable Mountain hotel
Maple Terrace Motel : 555 Main St.
+1-888-389-4485
555 Main St., Williamstown, MA 01267
+1-888-389-4485
~37.22 miles west of Chesterfield
- Pool in hotel: Beautiful secluded heated pool with amazing and breathtaking views.
Opens Daily 9 AM and closes at Dusk.
- Low Cost Rural property
Henniker Motel
+1-800-805-5223
61 Craney Pond Rd., Henniker, NH 03242
+1-800-805-5223
~40.32 miles east of Chesterfield
- Includes a pool: Heated indoor pool 8 AM - 10:00 PM
- Two-star Mountain hotel
Vacation Village in The Berkshires in Lanesborough
+1-888-469-4795
276 Brodie Mtn Rd., Lanesborough, MA 01237
+1-888-469-4795
~44.52 miles southwest of Chesterfield
- Pool available: 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.
- Three Star Mountain hotel
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