Chatham Holiday Rentals

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Holiday Rentals in Chatham

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

9.6 out of 10, Exceptional, (96)
"Great location"
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

8.6 out of 10, Excellent, (12)
"This rental home set the stage for an enjoyable getaway. It was well stocked with what we needed for a few days away (dish soap, toiletries, sponge, towels, bedding, etc.), and the pictures are accurate to the setup of the home. It is located in a beautiful location near a private beach and marina which were the highlight of our stay. The area was quiet and allowed for quality family time."
The price is AU$644
includes taxes & fees
15 July - 16 July
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (346)
"Very nice place to stay "
Holly Tree Resort

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (102)
"Overall good place to stay"
The price is AU$694
includes taxes & fees
14 July - 15 July
Brewster Green Resort

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (281)
"All around a great place to stay!"
The price is AU$758
includes taxes & fees
22 July - 23 July
Edgewater Beach Resort, a VRI resort

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (161)
"The property was very nice very clean beautiful area a lot of parking very nice when you walk in front desk was sweet Only thing they need a new play ground for the kids kinda old but other then that beautiful "
The price is AU$580
includes taxes & fees
31 July - 1 Aug
Riverview Resort

3 Mi to Beach: Historic Farmhouse on Cape Cod!

10.0 out of 10, Exceptional, (1)
"The house check-in process was very smooth and straightforward. The inside was freshly cleaned and painted with great Cape colors. Plenty of bedrooms and bathrooms for our party. The home has kept the old charm from being a nearly 200 yr old home but cleaned up with modern touches. "
The price is AU$1,263
includes taxes & fees
6 Aug - 7 Aug
3 Mi to Beach: Historic Farmhouse on Cape Cod!

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

10.0 out of 10, Exceptional, (155)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
The price is AU$603
includes taxes & fees
30 July - 31 July
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista

9.6 out of 10, Exceptional, (132)
"Spent a week at this nice condo in mid-January. Cozy and warm, right on the beach. The Cape in mid-winter is very quiet but that is what we had wanted. Our 15 year old Shih-Tzu was comfortable and happy. Nice relaxing week on this terrific property."
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

8.4 out of 10, Very good, (35)
"Perfect for one or two people, was great for myself and my dog to stay."
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

Steps to private Beach, Golf Course, AC, tandem Kayak for Guests

9.6 out of 10, Exceptional, (23)
"Enjoyed our stay: clean, modern and great location."
Steps to private Beach, Golf Course, AC, tandem Kayak for Guests

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (215)
"We really enjoyed our stay there and can definitely see staying there again. Very convenient to really everything you might want to do. Restaurants nearby as well as the beaches, beautiful places, and boardwalks over the marshes. Also, very clean and comfortable."
Steps to the Ocean! Perfect Location!!!

Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

2.0 star property
Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

Gorgeous Cottage steps from the beach

8.4 out of 10, Very good, (15)
"Great place to stay we loved it"
Gorgeous Cottage steps from the beach

Pristine bungalow with amazing walkable location - fast WiFi, firepit, & grill

8.4 out of 10, Very good, (29)
"We will stay here again -especially this time of year! It was absolutely prefect!"
Pristine bungalow with amazing walkable location - fast WiFi, firepit, & grill

Deluxe 2 Queens Size Beds Hotel Room in Yarmouth, 2 miles from Hyannis Main St.

9.0 out of 10, Wonderful, (2)
"Very nice and clean. Would definitely stay here again "
The price is AU$531
includes taxes & fees
14 July - 15 July
Deluxe 2 Queens Size Beds Hotel Room in Yarmouth, 2 miles from Hyannis Main St.

New Eastham Oceanside Guest Suite with Pool and Hot Tub

10.0 out of 10, Exceptional, (5)
New Eastham Oceanside Guest Suite with Pool and Hot Tub

NEW LISTING! Spacious Brewster Beach Retreat – Walk to Multiple Beaches!

10.0 out of 10, Exceptional, (1)
"We had a wonderful time in this cute cape cod beach house. The fenced in backyard is lovely and absolutely perfect for the family to gather after a day at the beach. The inside is very cozy and we were very comfortable here. Restaurants and beaches are very close by. Scoops (ice cream store) and the general store are exactly 1 mile away. The best part for us was the little beach that was about an 8 minute walk from the house. Cape cod beaches are hard to get into as the parking lots fill up...
NEW LISTING! Spacious Brewster Beach Retreat – Walk to Multiple Beaches!

THE BOAT HOUSE LOFT ~ RELAXING & PRIVATE WATERFRONT HOLIDAY ~ SHORT & LONG TERM

9.4 out of 10, Exceptional, (111)
"Great views of the pond. Perfect little spot for a getaway! We appreciated access to the kayaks and canoe to take advantage of Swan Pond and River. Owner was very kind and helpful throughout our stay. "
THE BOAT HOUSE LOFT ~ RELAXING & PRIVATE WATERFRONT HOLIDAY ~ SHORT & LONG TERM

Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks

9.8 out of 10, Exceptional, (173)
"Very happy with our stay"
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
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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Frequently asked questions

Can I find a holiday rental in Chatham?

Yes, there are holiday rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the popular beaches and waterfront in Chatham. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Chatham has to offer?

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK: This highly rated holiday home rental in Chatham is located on a river, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Chatham are Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK and Cozy Retreat in South Chatham (2374).

How many holiday rentals are there in Chatham?

With 294 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Atwood House Museum and Gallery Antonia, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Fish Pier and Chatham Lighthouse are other places worth a visit.

What are holiday rentals like in Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chatham. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.