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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Chatham holiday homes

TV, fireplace

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (102 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is £535
includes taxes & fees
14 Jul - 15 Jul
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Fridge, microwave, oven, stovetop

Luxury Chatham Retreat. Walk to Main St & Beach

Luxury Chatham Retreat. Walk to Main St & Beach
Chatham
10.0 out of 10, Exceptional, (1 review)
"Beautiful house in a great location in Chatham! Walking distance to shops and restaurants. The house was well-stocked with everything we needed and the beds were so comfortable. We really enjoyed our stay here!"
United States
Maggie K.
The price is £766
includes taxes & fees
30 Jun - 1 Jul
Luxury Chatham Retreat. Walk to Main St & Beach
Outdoor dining

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Chatham
10.0 out of 10, Exceptional, (136 reviews)
"Perfect location near shops, on the water. Spotlessly clean, comfortable beds, well equipped kitchen, and very responsive hosts. This was a perfect spot for our multigenerational family vacation. "
United States
Maggie N.
The price is £2,152
includes taxes & fees
18 Jul - 19 Jul
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
TV, offices

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"We loved the house. Simple and comfortable, exactly what we needed to relax. thank you."
United States
Michael M.
The price is £522
includes taxes & fees
29 Jun - 30 Jun
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Outdoor dining

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Dennis Port
The price is £345
includes taxes & fees
30 Jun - 1 Jul
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Outdoor dining

Relaxing Cape Cod Cottage Getaway

Relaxing Cape Cod Cottage Getaway
Dennis
The price is £457
includes taxes & fees
29 Jun - 30 Jun
Relaxing Cape Cod Cottage Getaway
Dining

Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (19 reviews)
"Very clean, great place for kids!"
United States
Ruth
The price is £289
includes taxes & fees
29 Jun - 30 Jun
Cape Cod's "Beach Rose"
TV, DVD player, offices

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (24 reviews)
"Loved this property. "
United States
Carol S.
The price is £397
includes taxes & fees
15 Jul - 16 Jul
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Smart TV, fireplace

Coastal Haven in West Dennis

Coastal Haven in West Dennis
Dennis
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay and relax, just a short walk to the beach and quick drive to great restaurants and activities. Highly recommend!!"
United States
Melissa J.
The price is £547
includes taxes & fees
29 Jun - 30 Jun
Coastal Haven in West Dennis
TV

Family-Friendly Home! Walk to Sea Street Beach

Family-Friendly Home! Walk to Sea Street Beach
Dennis Port
7.0 out of 10, Good, (2 reviews)
"Location was great! Cozy house. Easy to get in touch with host. Bathroom could use update. "
United States
Devin L.
The price is £245
includes taxes & fees
29 Jun - 30 Jun
Family-Friendly Home! Walk to Sea Street Beach
Fridge, microwave, oven, stovetop

Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...
United States
Bethany P.
The price is £529
includes taxes & fees
9 Jul - 10 Jul
Entire Hyannis Home - Near Downtown & Beaches
Outdoor dining

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
10.0 out of 10, Exceptional, (193 reviews)
"Good location, pet friendly and clean"
United States
Megan R.
The price is £278
includes taxes & fees
1 Jul - 2 Jul
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Interior

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Charming Cape Escape with Pool, Hot Tub & Fire Pit
South Dennis
10.0 out of 10, Exceptional, (1 review)
"This was a lovely home perfect for a summer stay!"
United States
John and Jenny A.
Charming Cape Escape with Pool, Hot Tub & Fire Pit
Outdoor dining

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Driftmoor~Dog Frndly 3bd/2 bth~Luxe
Eastham
10.0 out of 10, Exceptional, (1 review)
"We stayed here two nights while exploring cape cod on a family vacation. The house was beautiful, clean, beds were comfortable and it was pet friendly. The cookies and dog bones were a nice surprise when we arrived. Arrival and departure Instructions were clear and communication with Tara was excellent. Tara provided a lot of information about the area. The neighborhood was nice and quiet and getting in and out was easy. I would definitely stay here again. Thanks Tara! "
United States
Diane G.
Driftmoor~Dog Frndly 3bd/2 bth~Luxe
TV, fireplace, books

10 min walk to Beach - Home with Amazing View & Huge Deck

10 min walk to Beach - Home with Amazing View & Huge Deck
Eastham
The price is £635
includes taxes & fees
5 Jul - 6 Jul
10 min walk to Beach - Home with Amazing View & Huge Deck
Beach

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Barnstable
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
The price is £587
includes taxes & fees
30 Jun - 1 Jul
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Terrace/patio

New! 4BR Fire Pit, Ping Pong, Movie Room

New! 4BR Fire Pit, Ping Pong, Movie Room
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"Very responsive and friendly host. "
United States
Matt M.
The price is £1,017
includes taxes & fees
7 Jul - 8 Jul
New! 4BR Fire Pit, Ping Pong, Movie Room
On the beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (31 reviews)
"The house is adorable. Great location. Would love to stay again!"
United States
Laura G.
Sand Bar-Dog Friendly on Cooks Brook Beach
Property grounds

Pond Access, Fire Pit & Bikes, house with AC in charming Brewster

Pond Access, Fire Pit & Bikes, house with AC in charming Brewster
Brewster
The price is £969
includes taxes & fees
30 Jun - 1 Jul
Pond Access, Fire Pit & Bikes, house with AC in charming Brewster
Smart TV, fireplace

The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (23 reviews)
"Our host was very responsive and all the instructions were clear. The house was immaculate and a perfect spot of a winter getaway. Would stay again!"
United States
Anna P.
The price is £718
includes taxes & fees
26 Jul - 27 Jul
The Pet-Friendly Surf Shack Hideaway on the Cove
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.
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Top Chatham Hotel Reviews

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Hotel was great from the room to Goose Tavern Restaurant! Room was spacious and comfortable with all conveniences. Daily continental breakfast was very good! Staff was very friendly and helpful! Pool was much smaller than expected. Location was perfect for walking in Chatham. Easy drive to Ferry to Martha’s Vineyard and Nantucket. Would definitely recommend and stay again!"
John 4-night trip
Posted less than an hour ago
Chatham Wayside Inn

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
494
Accommodation
2597 Holiday Homes
Lowest Price
£245
Highest Price
£2,152