Chatham Hotels with Pools - Outdoor/Indoor Pools in Chatham MA

Chatham 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 Chatham, MA for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Chatham Massachusetts hotel and motel rooms for children. Review the list of Chatham hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.
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Chatham Hotels with Outdoor or Indoor Pools

The Chatham Motel 1487 Main Street, Chatham, MA 02633 +1-888-389-4121
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from July to September. Pool access available from 9:00 AM to 8:00 PM.
  • 2 star Motel hotel
  • Check-in: 3:00 PM - 7:00 PM
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Greyfinch Chatham Inn 946 Main Street, Chatham, MA 02633 +1-888-675-2083
  • Pool available: Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June to September.
  • Three Star Motel property
  • Check-in time: 4:00 PM - 7:00 PM
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Queen Anne Inn 70 Queen Anne Rd, Chatham, MA 02633 +1-800-716-8490
  • Pool in hotel: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May to September.
  • Four star property
  • 2 floors in hotel
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Very Good 8.6 /10 Hotel Reviews Call BookMore Details
Chatham Wayside Inn 512 Main St, Chatham, MA 02633 +1-800-805-5223
  • Pool details: Pool umbrellas, Swimming pool, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June to September. Pool access available from 8 AM to 8 PM.
  • Four-star property
  • 56 rooms in hotel
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
Chatham Seafarer Inn 2079 Main St, Chatham, MA 02633 +1-888-965-1860
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from May to September. Pool access available from 8 AM to 8 PM.
  • Affordable property
  • 22 rooms in property
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Excellent 9.0 /10 Read Reviews Call BookMore Details
Chatham Bars Inn 297 Shore Rd, Chatham, MA 02633 +1-888-788-5576
  • Pool available: Swimming pool, Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from April to October. Pool access available from 9:00 AM to 5 PM.
  • Luxury 5 star Resort hotel
  • 3 floors in property
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Excellent 9.2 /10 Recent Reviews Call BookMore Details
Pleasant Bay Village Resort 1191 Orleans Road, Chatham, MA 02633 +1-888-897-9207
  • Includes a pool
  • 3 star property
  • 58 rooms in hotel
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Excellent 10.0 /10 Guest Reviews Call BookMore Details
Wequassett Resort and Golf Club 2173 Head of the Bay Rd. Route 28, Harwich, MA 02645 +1-888-311-4278 ~2.53 miles north of Chatham
  • Has swimming pool: Pool umbrellas, Outdoor seasonal pool, Pool cabanas (surcharge), Pool sun loungers. The seasonal pool will be open from March to November.
  • Luxurious Five Star Resort hotel
  • Hotel has a green policy Learn more
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Excellent 9.2 /10 Review Score Call BookMore Details
Handkerchief Shoals Inn 888 Route 28, South Harwich, MA 02661 +1-888-469-4795 ~3.52 miles west of Chatham
  • Pool in hotel: Outdoor seasonal pool.
  • 3 star Motel hotel
  • Check-in: 3:00 PM - 8:00 PM
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Very Good 8.6 /10 Hotel Reviews Call BookMore Details
Wychmere Beach Club 23 Snow Inn Road, Harwich Port, 02646 +1-888-734-9421 ~4.74 miles west of Chatham
  • With a pool!
  • Economy hotel
  • Check in time: 15:00:00 - 23:30:00
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Excellent 9.4 /10 Hotel Reviews Call BookMore Details
Harwichport Resort Club 558 Massachusetts 28, Harwich, MA MA02646 +1-888-841-5292 ~5.01 miles west of Chatham
  • Includes a swimming pool
  • Four star Resort property
  • Check in: 16:00:00 - 20:00:00
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Pelham on Earle 30 Earle Rd, West Harwich, MA 02671 +1-888-455-5160 ~6.32 miles west of Chatham
  • Has swimming pool: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May 27 to October 31.
  • Three Star hotel
  • 27 rooms in hotel
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
Skaket Beach Motel 203 Cranberry Hwy, Orleans, MA 02563 +1-888-965-8297 ~6.44 miles north of Chatham
  • Pool available: Swimming pool, Outdoor seasonal pool. The seasonal pool will be open from June to October. Pool access available from 9 AM to 8 PM.
  • Inexpensive Motel property
  • 43 rooms in property
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Olde Tavern Motel & Inn 151 Cranberry Hwy, Orleans, MA 02653 +1-888-906-6358 ~6.67 miles north of Chatham
  • Pool available: Pool sun loungers. The seasonal pool will be open from June 01 to September 06.
  • Midscale Motel hotel
  • 2 floors in property
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Excellent 9.0 /10 Latest Reviews Call BookMore Details
A Beach Breeze Inn 169 Route 28, West Harwich, MA 02671 +1-888-749-6785 ~6.69 miles west of Chatham
  • Pool in hotel: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May 22 to September 28.
  • Mid-scale Motel property
  • Check in: 3:00 PM - 8:00 PM
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Excellent 9.6 /10 Hotel Reviews Call BookMore Details
The Villages at Ocean Edge One Villages Drive, Brewster, MA 02631 +1-888-878-9982 ~6.76 miles northwest of Chatham
  • Pool in hotel: Wheelchair-accessible pool, Children's pool.
  • Mid-scale Resort property
  • 245 rooms in hotel
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Very Good 8.4 /10 Latest Reviews Call BookMore Details
Charm on Main by Ocean Edge 2553 Main Street, Brewster, MA 02631 +1-888-389-4485 ~6.88 miles northwest of Chatham
  • Includes a pool: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Access to nearby outdoor pool, Fence around pool. The seasonal pool will be open from May 20 to October 31.
  • Economy hotel
  • 3 floors in property
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The Mansion at Ocean Edge 2907 Main Street, Brewster, MA 02631 +1-888-389-4121 ~6.95 miles northwest of Chatham
  • Has swimming pool: Outdoor seasonal pool, Children's pool, Pool sun loungers.
  • Expensive property
  • 121 sleeping rooms in hotel
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The Cove Motel 13 South Orleans Road, Orleans, 02653 +1-888-675-2083 ~7.10 miles north of Chatham
  • Has swimming pool
  • Mid-scale Motel hotel
  • Check in time: 15:00:00 - 21:00:00
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Rodeway Inn Orleans - Cape Cod 48 Cranberry Hwy, Orleans, MA 02653 +1-800-716-8490 ~7.29 miles north of Chatham
  • Includes a pool: Outdoor seasonal pool. The seasonal pool will be open from May to September. Pool access available from 8:00 AM to 8:00 PM.
  • 2 star Motel property
  • Check in time: 3:00 PM - midnight
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The Corsair & Cross Rip Oceanfront Resort 41 Chase Ave, Dennis Port, MA 02639 +1-800-805-5223 ~7.65 miles west of Chatham
  • Pool available: Pool umbrellas, Pool toys, Pool sun loungers, Fence around pool.
  • Affordable hotel
  • Check in: 4:00 PM - 9:00 PM
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Very Good 8.6 /10 Guest Reviews Call BookMore Details
Bluebird Dennisport 426 Lower County Rd, Dennis Port, MA 02639 +1-888-965-1860 ~7.65 miles west of Chatham
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from June 01 to September 30.
  • Three Star property
  • Pet-friendly
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Colonial Village 426 Lower County Rd., Dennis Port, 2639 +1-888-788-5576 ~7.65 miles west of Chatham
  • With a pool!
  • Low Cost hotel
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The Three Seasons Resort 421 Old Wharf Rd, Dennis Port, 02639 +1-888-897-9207 ~7.82 miles west of Chatham
  • Has swimming pool
  • Low Cost Resort hotel
  • Check-in time: 15:00:00 - 00:00:00
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Average 7.8 /10 Recent Reviews Call BookMore Details
Jonathan Edwards Motel 393 Main St, Dennis Port, MA 02639 +1-888-311-4278 ~7.99 miles west of Chatham
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from May 23 to September 09.
  • Economy property
  • Check in time: 3:00 PM - 6:30 PM
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Holiday Hill Inn & Suites 352 Main Street, Dennis Port, MA 02639 +1-888-469-4795 ~8.10 miles west of Chatham
  • Pool details: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May 01 to October 09.
  • 2-star Motel hotel
  • Check-in: 3:00 PM - midnight
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Very Good 8.4 /10 Review Score Call BookMore Details
Doryman Motel 73 Sea Street, Dennis Port, MA 02639 +1-888-734-9421 ~8.11 miles west of Chatham
  • Pool available: Outdoor seasonal pool. The seasonal pool will be open from June to September.
  • Economy Motel hotel
  • Hotel has 34 rooms
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Excellent 9.6 /10 Recent Reviews Call BookMore Details
Dennis Port Surf Club (Boutique Hotel) 329 Main Street, Dennis Port, MA 02639 +1-888-841-5292 ~8.15 miles west of Chatham
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from June to September.
  • 3 star Motel hotel
  • Pets Allowed
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Pelham House Resort 14 Sea Street, Dennis Port, MA 02639 +1-888-455-5160 ~8.25 miles west of Chatham
  • We have a pool
  • Affordable Resort property
  • Hotel has 3 floors
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Kingfisher Oceanside 15 Sea St, Dennis Port, MA 026392414 +1-888-965-8297 ~8.27 miles west of Chatham
  • Includes a pool: Outdoor seasonal pool. The seasonal pool will be open from June to September.
  • Cheap Motel hotel
  • 16 rooms in property
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Eagle Wing Inn - Cape Cod 960 State Highway Route 6, Eastham, MA 02642 +1-888-906-6358 ~8.40 miles north of Chatham
  • Pool details: Outdoor seasonal pool, Pool sun loungers.
  • Mid-scale Motel hotel
  • 19 sleeping rooms in hotel
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Love Farms Lodge 829 Main Street, West Dennis, MA 02670 +1-888-749-6785 ~8.96 miles west of Chatham
  • Pool available: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June to October.
  • Affordable hotel
  • Check in: 3:00 PM - 9:00 PM
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Lighthouse Inn 1 Lighthouse Inn Rd, West Dennis, MA 02670 +1-888-878-9982 ~10.07 miles west of Chatham
  • Has swimming pool: Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June to October. Pool access available from 8:00 AM to 8:00 PM.
  • 3-star hotel
  • 68 sleeping rooms in hotel
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Very Good 8.8 /10 Reviews Call BookMore Details
GuestLodge 221 Main Street, West Dennis, MA 02670 +1-888-389-4485 ~10.09 miles west of Chatham
  • With a pool!
  • Economical Motel hotel
  • Check in: 3:00 PM - 6:00 PM
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Blue Rock Resort 39 Todd Rd, South Yarmouth, MA 02664 +1-888-389-4121 ~10.21 miles west of Chatham
  • Includes a pool: Pool umbrellas, Swimming pool, Wheelchair-accessible pool, Outdoor seasonal pool, Access to nearby indoor pool, Pool sun loungers, Access to nearby outdoor pool. The seasonal pool will be open from April to October. Pool access available from 7:30 AM to 8:00 PM.
  • 3 star property
  • Pet-friendly
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Very Good 8.6 /10 Guest Reviews Call BookMore Details
Travelodge by Wyndham Cape Cod Area 99 Main St, West Dennis, MA 02670 +1-888-675-2083 ~10.31 miles west of Chatham
  • We have a pool ready for use
  • 2-star property
  • Hotel has 2 floors
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Average 7.4 /10 Guest Reviews Call BookMore Details
Sesuit Harbor House 1421 Main Street, Dennis, MA 02641 +1-800-716-8490 ~10.38 miles west of Chatham
  • Pool available: Outdoor seasonal pool, Children's pool. The seasonal pool will be open from May to October.
  • 3 star property
  • Check in: 3:00 PM - 8:00 PM
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Excellent 9.6 /10 Hotel Reviews Call BookMore Details
Ambassador Inn & Suites 1314 Route 28, South Yarmouth, MA 02664 +1-800-805-5223 ~10.76 miles west of Chatham
  • Pool details: Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May to September. Pool access available from 9:00 AM to 9:00 PM.
  • Midscale property
  • Check-in time: 4:00 PM - anytime
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Endless Dunes a Modern Motel 3620 State Highway, Eastham, MA 02642 +1-888-965-1860 ~10.81 miles north of Chatham
  • Includes a pool: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June 06 to September 27. Pool access available from 8:00 AM to 6:00 PM.
  • Low Cost Motel hotel
  • 30 rooms in property
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Four Points by Sheraton Eastham Cape Cod 3800 State Hwy, Eastham, MA 02642 +1-888-788-5576 ~10.99 miles north of Chatham
  • Pool details: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May 27 to October 10.
  • Affordable hotel
  • Hotel has 2 floors
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Very Good 8.2 /10 Guest Reviews Call BookMore Details
Veranda Cape Cod Family Resort 1261 Route 28, South Yarmouth, MA 02664 +1-888-897-9207 ~11.00 miles west of Chatham
  • Pool available: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from June to September. Pool access available from 9:00 AM to 7:00 PM.
  • Mid-scale Motel hotel
  • Check in: 3:00 PM - 8:00 PM
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Excellent 9.5 /10 Latest Reviews Call BookMore Details
Ocean Park Inn 3900 State Highway, Eastham, MA 02642 +1-888-311-4278 ~11.01 miles north of Chatham
  • Pool available: Pool umbrellas, Swimming pool, Outdoor seasonal pool, Access to nearby indoor pool, Pool sun loungers. The seasonal pool will be open from May to September. Pool access available from 8:00 AM to 10:00 PM.
  • Two star Motel hotel
  • 54 rooms in hotel
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Average 7.0 /10 Recent Reviews Call BookMore Details
The Escape Inn 1237 Massachusetts Route 28, South Yarmouth, MA 02664 +1-888-469-4795 ~11.08 miles west of Chatham
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Low Cost hotel
  • 2 floors in property
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All Seasons Resort Trademark Collection by Wyndham 1199 Route 28, South Yarmouth, MA 02664 +1-888-734-9421 ~11.16 miles west of Chatham
  • Has swimming pool: Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May to October. Pool access available from 8:30 AM to 9:30 PM.
  • Mid-scale hotel
  • Free comp. breakfast
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Very Good 8.1 /10 Recent Reviews Call BookMore Details
Kingfisher Lodging 177 Rte 6A, Dennis, MA 02638 +1-888-841-5292 ~11.35 miles west of Chatham
  • Pool in hotel: Outdoor seasonal pool. The seasonal pool will be open from June to September.
  • 3-star Motel property
  • Check-in time: 4:00 PM - anytime
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Ocean Club on Smugglers Beach 329 South Shore Dr, South Yarmouth, MA 02664 +1-888-455-5160 ~11.76 miles west of Chatham
  • Includes a pool: Pool hoist on site, Wheelchair-accessible pool. Pool access available from 9 AM to 10 PM.
  • Affordable hotel
  • Fitness center on property
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Excellent 9.2 /10 Reviews Call BookMore Details
Riviera Beach Resort 327 South Shore Drive, South Yarmouth, MA 02664 +1-888-965-8297 ~11.83 miles west of Chatham
  • Pool in hotel: Pool umbrellas, Wheelchair-accessible pool, Outdoor seasonal pool, Children's pool, Access to nearby indoor pool, Pool sun loungers. The seasonal pool will be open from May to October. Pool access available from 9:00 AM to 9:00 PM.
  • Affordable property
  • 125 sleeping rooms in hotel
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Blue Water Resort 291 South Shore Dr, South Yarmouth, MA 02664 +1-888-906-6358 ~11.89 miles west of Chatham
  • Pool in hotel: Pool umbrellas, Wheelchair-accessible pool, Outdoor seasonal pool, Access to nearby indoor pool, Pool sun loungers. The seasonal pool will be open from May to October. Pool access available from 9:00 AM to 9:00 PM.
  • Midscale Resort property
  • Fitness / Gym is on-site
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Very Good 8.4 /10 Review Score Call BookMore Details
Surf & Sand Beach Motel 277 South Shore Drive, South Yarmouth, 02664 +1-888-749-6785 ~11.95 miles west of Chatham
  • We have a pool
  • 3-star hotel
  • Check-in: 15:00:00 - 21:00:00
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Cape Cod Motor Inn 890 Massachusetts 28, South Yarmouth, MA 02664 +1-888-878-9982 ~12.15 miles west of Chatham
  • Has swimming pool: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May 23 to September 17. Pool access available from 9:00 AM to 8:00 PM.
  • 3 star Motel hotel
  • Check in: 3:00 PM - 8:00 PM
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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863 a service by Reservations.ai
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