Book Guest Houses in Chatham, MA

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Top Guest Houses in Chatham

Winstead Inn

116 Parallel, Harwich, MA

$224 nightly

$257 total

Oct 23 - Oct 24

Total with taxes and fees

A seasonal outdoor pool, free self parking, and concierge services are featured at this guesthouse. Take the free beach shuttle and relax with sun loungers and beach umbrellas. Enjoy freebies like self-serve breakfast and a beach shuttle

Pool

Breakfast included

The Rugosa Guest House

4885 US-6, Eastham, MA

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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and a picnic area are also on offer.

Sea Breeze Inn

270 Ocean Avenue, Hyannis, MA

$79 nightly

$90 total

Oct 23 - Oct 24

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-out, and luggage storage are also on offer.

Parking included

Free WiFi

By the Sea Guests Bed & Breakfast & Suites

57 Chase Avenue & Inman Road Extension, Dennis Port, MA

$231 nightly

$264 total

Oct 23 - Oct 24

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

On private beach

Parking included

The Seagrove Suites & Guest Rooms

25 Seaview Rd, Eastham, MA

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A seasonal outdoor pool, free self parking, and concierge services are featured at this guesthouse. WiFi in public areas is free. A garden, a picnic area, and express check-in are also on offer.

Pool

Pet friendly

Fleetwing Guest House

158 Riverside Dr, West Harwich, MA

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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a picnic area, and barbecue grills are also on offer.

Pet friendly

Parking included

Beach family gateway, modern 5BR, walk to the beach, big yard, firepit

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Stay at this guesthouse in Dennis Port. Enjoy free WiFi and air conditioning. Popular attractions Haigis Beach and Sea Street Beach are located nearby.

Free WiFi

Air conditioning

Newly furnished-Enjoy sun drenched days w/ gentle breezes & fragrant salt air

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This guesthouse features a garden, laundry facilities, and barbecue grills.

Air conditioning

Parking available

Bright & Cozy with Patio, Grill and near the Beach & Golf

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This guesthouse features a garden, laundry facilities, and barbecue grills.

Free WiFi

Air conditioning

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top hotels in Chatham

Chatham Wayside Inn

512 Main St, Chatham, MA

$196 nightly

$224 total

Nov 5 - Nov 6

Total with taxes and fees

9.2/10 Wonderful! (576 reviews)

Chatham Guest Houses essential information

Accommodation	9 Guest Houses
Lowest Price	$90
Highest Price	$455
Popular accommodation	Winstead Inn, The Rugosa Guest House, Sea Breeze Inn, By the Sea Guests Bed & Breakfast & Suites, The Seagrove Suites & Guest Rooms, Fleetwing Guest House, Beach family gateway, modern 5BR, walk to the beach, big yard, firepit, Newly furnished-Enjoy sun drenched days w/ gentle breezes & fragrant salt air, Bright & Cozy with Patio, Grill and near the Beach & Golf