
Holiday rentals with breakfast in Chatham
Find and book unique rentals with breakfast on Airbnb
Top-rated rentals with breakfast in Chatham
Guests agree: these breakfast rentals are highly rated for location, cleanliness and more.

Centrally located 3 Bedroom w Large Deck private
This charming Cape-style ranch is perfectly situated close to popular Cape Cod attractions. It features 3 bedrooms—two with queen beds and one with twins. Recently renovated, the home boasts a modern kitchen with granite countertops. Central air conditioning ensures comfort during warm, humid nights. Nestled in a quiet, friendly neighborhood, it offers easy access to all the Cape’s highlights. Enjoy meals outdoors on the spacious deck with a large eating area—ideal for relaxing and entertaining.

Step Away; A Martha's Vineyard Retreat
Studio apartment addition attached to our family home. Our home is located three miles to downtown Edgartown with bus service & bike path close by. Private entrance, mini fridge, coffee press & accessories, private bath with shower, washer/dryer, bed in a loft area (ladder access only) with queen size sofa bed available below for additional sleeping. This is our family home with two baby boys. We try our best to keep quiet, but it is important to note their presence; rental has a sound machine.

Cape Diem| 1.5M to Craigville Beach| 4 Beds,2 Bath
Coastal Retreat in West Hyannisport– Relax & Unwind! Escape to Cape Diem, a beautifully renovated home just minutes from Craigville & Covell’s Beach! Brand new furniture in all rooms and outside, a full kitchen, and game/media room. Outside, enjoy a spacious fenced-in backyard with pergola, grill, & fire pit—perfect for laid-back evenings. Close to Melody Tent & Hyannis Main Street, you’ll have easy access to charming shops, restaurants, and entertainment. Experience Cape Time at its finest!

Claw Foot Tub & King Bed at Club Tanuki Cottage
Glorious gardens and bay breezes! King-sized Casper bed in romantic antique Cape Cod studio cottage with private entrance & patio, in-room double-slipper claw foot tub, luxe bath amenities, Brooklinen sheets. Just renovated soup-to-nuts! Marble & antique wooden floors, decorated with rotating collection of antiques, original local art & great light. Nestled along historic route 6A (Main Street) near other galleries, museums, walking trails, ponds and beaches; 90 seconds to closest beach.

East Chop Cottage - walk to lighthouse & beach!
This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

A little bit of "heaven" in Dennis
Quiet and relaxing oasis -Enjoy your stay in this bright newly remodeled studio with updated WiFi extender and plenty of natural lighting. This inviting space is centrally located in a lovely neighborhood with free parking. Enjoy the private backyard patio, outdoor shower and nearby walking path, as well as easy access to shopping and restaurants just minutes away. Best of all, relax at some of the most beautiful north side beaches that the Cape has to offer less than 5 miles away!

“Rising Sun Cottage” 2 bdrms, Center of Town!
The Rising Sun", "Cottage #1 at the John Randall House" is a spacious, fully furnished two-bedroom condo. Located in the center of town, yet quiet and secluded. The Cottage comes with on-site parking for 2 vehicles, split system heating and air, washer/dryer, a front deck with gas grill on site, a recently updated full kitchen, Master Bedroom with King bed, and much more. Recently renovated, this beautifully decorated home is part art gallery with a sophisticated boutique feel.

New Seabury French Chateau Inspired
You will love this bright, sunny, safe, quiet and fully fenced New Seabury home for home away getaway and relaxation. Split floor plan with master bedroom and bath on one side of the home, while there are two other bedrooms which share a bath on the other side. All bedrooms are large enough to accommodate family of 10! Additional living space in the loft as well as a bedroom and bath in the basement. Less than a mile away from the beach, lots of beautiful trails and more!

Cottage at the Escape Inn
Guests will have a special experience as this cottage provides a fireplace. Featuring a private entrance, this air-conditioned cottage is consisted of 1 living room, 2 separate bedrooms and 1 bathroom with a bath and a shower. The well-equipped kitchen features a stovetop, a refrigerator, a dishwasher and kitchenware. The spacious chalet offers a tea and coffee maker, a seating area, a wardrobe, a sofa, as well as a flat-screen TV with cable channels. The unit offers 3 beds.

Cape EsCape:2 Rm Private Suite, EZ walk to beaches
Magical ALL year ‘round. location, Location, LOCATION; comfy, contemporary newly renovated (‘21) private bedrm & family rm 0.4mile from neighborhd river-beach, 0.9mi from row of ocean beaches, hiking trails, live theater, everywhere. Separate private entrance. A/C. Queen bed. Outside space with picnic table, chairs, & hammock. Beach chairs provided. W/in 5 min walking distance of bakeries, mini-golf, restaurants, shopping, bike trail, kayaking, & more.

Walk to Town/Golf Club - Renovated Edgartown Home
Location, location, location! The perfect Martha’s Vineyard retreat—walk to downtown Edgartown! Ideally located on a quiet street off Upper Main, just a 10-minute stroll to shops, restaurants, and near Edgartown Golf Club. Minutes to scenic bike paths and beaches. This fully renovated 2BR/2BA home features a new kitchen, bathrooms, furnishings, and comfortably sleeps 5.

The Beach House - WALK to BEACH with total privacy
This is such a special place! Privacy like this is hard to find anywhere. Come and enjoy the peace and quiet this property offers on a dead-end road. Walk to First Encounter Beach! Voted one of the BEST bayside beaches annually!! Ride your bike to Orleans or Wellfleet on the bike trail. Or, just enjoy the lovely patio and outdoor fireplace.
Popular amenities for rentals with breakfast in Chatham
House rentals with breakfast

Lakefront Chatham Home w kayaks. 5 Min to beach!

Spacious contemporary villa near beach and village

Stunningly renovated 4Bed/3Bath Ocean Front home!

Ebb Tide~Dog Frndly/3bd 2bth/Walk to Water

Best little house in Chatham!

Knotical Cottage newly renovated, Dogs welcomed

Ocean Harbor Estates

New 2026 Beautifully Curated Orleans Retreat Close
Apartment rentals with breakfast

Beach Walk to Dennis Port beach/restaurants/Bars

Beautiful private spacious apartment

The Mainstay at Menemsha Inn

Peaceful spot near amazing beaches and seafood!

Carriage House Studio: pet-friendly near village!
Bed and breakfast rentals with breakfast

Captain R03 - Small room, Queen bed & Private bath

“AT HYDRANGEA FARM” Bed and Breakfast

#4 (1 King Bed with Private Bath in room)

North Falmouth Suite 'downstairs suite'

Outer Cape Escape 1 BR B&B INCLUDES BREAKFAST

Sweet stay by the ocean w breakfast (1 of 2 rooms)

Howards End - Room 2-1 (Queen Bed & Private Bath)

#7 location location location, pool private room
Quick stats about holiday rentals with breakfast included in Chatham

Total holiday rentals
Explore 20 holiday rentals in Chatham

Nightly prices starting at
Chatham holiday rentals start at £81 per night before taxes and fees

Verified guest reviews
Over 2,010 verified reviews to help you choose

Wifi availability
20 of Chatham holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chatham rentals

4.7 Average rating
Chatham stays receive an average rating of 4.7 out of 5 from guests
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- Cape Cod
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