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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 2522 Vacation Homes in Chatham with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (89)
"Beautiful home! Check in was easy. I had a quick question and the host answered very promptly and was super nice ! House was very clean and the electric fireplace was a plus! We will definitely stay here again! "
The price is AED 415
AED 1,659 total
includes taxes & fees
16 Apr - 17 Apr
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Outdoor spa tub

WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

10.0 out of 10, Exceptional, (84)
"House was just as it looked in pictures. Great yard and hot tub. Close to all the cape has to offer. Will stay again !"
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Sand Bar-Dog Friendly on Cooks Brook Beach
Fridge, microwave, oven, stovetop

Sand Bar-Dog Friendly on Cooks Brook Beach

10.0 out of 10, Exceptional, (15)
"Hope to be back soon!"
The price is AED 816
AED 1,990 total
includes taxes & fees
1 Apr - 2 Apr
Sand Bar-Dog Friendly on Cooks Brook Beach
Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach
TV, books

Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

8.0 out of 10, Very Good, (9)
"We plan to come back. This was a great place for 3 couples. We had a little problem with bugs but nothing we couldn’t handle. Close to the bay and everything we wanted. Definitely a good experience. Recommend"
Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
Exterior

OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

10.0 out of 10, Exceptional, (103)
"Host was always responsive. Property was even better than listing pictures. Location cannot be beat. The perfect gathering place for our Fall Friends Getaway. Already booked for next year! "
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
Secluded home with firepit, & scenic yard - near Nauset Beach & shops
Exterior

Secluded home with firepit, & scenic yard - near Nauset Beach & shops

8.0 out of 10, Very Good, (37)
"I had a great Labor Day weekend here with my family. The house was very clean and very close to Nauset Light Beach. I would definitely stay here again."
Secluded home with firepit, & scenic yard - near Nauset Beach & shops
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Miscellaneous

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

10.0 out of 10, Exceptional, (150)
"Perfect for our stay, comfortable beds, well stocked kitchen very clean, easy to communicate with owner, nice that it is pet friendly"
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Waterfront, Incredible Views and Private Dock!
Interior

Waterfront, Incredible Views and Private Dock!

9.4 out of 10, Exceptional, (3)
"Location was great for us. Beds were very clean and comfortable and many bedrooms. Kitchen view was amazing and appliances worked well. Overall, very nice, quiet vacation home. "
Waterfront, Incredible Views and Private Dock!
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Outdoor dining

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed our stay! The house is lovely! An easy walk to downtown shops and restaurants and a beautiful neighborhood as well! Lisa and Brian are wonderful hosts and are available with anything you may need. A true gem for your Chatham stay!"
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Interior

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (108)
"Absolutely gorgeous location with amazing views and lots of privacy in the winter. Will stay again!"
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Cozy Yarmouth Cottage
Property grounds

Cozy Yarmouth Cottage

9.6 out of 10, Exceptional, (5)
"Beautiful and comfortable space perfect for our family of four. "
The price is AED 411
AED 1,022 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Yarmouth Cottage
Close to Bike Path 1 Mile to Beaches!
Beach nearby

Close to Bike Path 1 Mile to Beaches!

9.6 out of 10, Exceptional, (16)
"Great place to use as a base to explore Cape Cod. Well stocked, clean, and quiet. Had some problem with the TV, but the company responded quickly and had someone out to fix it right away. "
Close to Bike Path 1 Mile to Beaches!
Brewster Pond Front Perfection, Walk to Private Beach: 239-B
Fridge, microwave, oven, stovetop

Brewster Pond Front Perfection, Walk to Private Beach: 239-B

10.0 out of 10, Exceptional, (5)
"Wonderful Location, close to the ferry at Hyannis. Centrally located on the Cape. The view over Brewster Pond is amazing. House is wonderfully done and furnished. "
Brewster Pond Front Perfection, Walk to Private Beach: 239-B
Hot Tub, 200 ft to Beach!
Outdoor dining

Hot Tub, 200 ft to Beach!

10.0 out of 10, Exceptional, (6)
"Very comfortable, clean home Nice location and hot tub was awesome!! "
Hot Tub, 200 ft to Beach!
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub
Sun loungers, beach towels

Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub

10.0 out of 10, Exceptional, (143)
"We had a great time at this beautiful beachy getaway. Our dogs LOVED the fenced in backyard! The hosts thought of everything so all we had to do was enjoy. "
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub
Oakwood Trail Cottage | Eastham home on Cape Cod Rail Trail with great deck
Terrace/patio

Oakwood Trail Cottage | Eastham home on Cape Cod Rail Trail with great deck

8.0 out of 10, Very Good, (5)
"The place was not good the plumbing did work on the second floor. It smelled like pee and someone had left the AC unit in the tub."
Oakwood Trail Cottage | Eastham home on Cape Cod Rail Trail with great deck
Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food
Smart TV, fireplace, DVD player, foosball

Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food

9.8 out of 10, Exceptional, (131)
"We very much enjoyed our stay over the winter holidays! "
Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food
Charming 3-bedroom house in East Dennis with beautiful pool & jacuzzi
Miscellaneous

Charming 3-bedroom house in East Dennis with beautiful pool & jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (1)
"We really enjoyed this cozy home! It was tastefully decorated with a beachy vibe and very well equipped. The owner was responsive and easy to communicate with. I mentioned we were staying for our 20th anniversary and they even left a bottle of champagne. Everything was clean and comfortable. We enjoyed both the hot tub and fire pit. The location was perfect for us. Highly recommend! "
Charming 3-bedroom house in East Dennis with beautiful pool & jacuzzi
Escape The Commotion - Relax By The Ocean
Beach

Escape The Commotion - Relax By The Ocean

9.8 out of 10, Exceptional, (65)
"The house was older, but the kitchen and bathrooms were updated. The house was perfect for our family. Close to the beach, shopping and attractions, but in a quiet neighborhood. Overall, we really enjoyed our stay. Couldn’t find the washer &dryer until the last day of our stay because they were tucked away in a bedroom closet. Would have liked to know that on day one. "
Escape The Commotion - Relax By The Ocean
Seaside Retreat w/ Private Beach Landing!
Terrace/patio

Seaside Retreat w/ Private Beach Landing!

9.8 out of 10, Exceptional, (11)
"Fantastic Ladies Weekend!!!! Cutest house on the most beautiful spot! Smooth communication with management company. House was clean and beautiful. The beds were extremely comfortable. Hot tub was clean and hot!!! Outdoor shower was perfect with hot hot water and great water pressure.!! Very Dog friendly remote space to roam and neighbors dogs were friendly! I did not want to leave. "
Seaside Retreat w/ Private Beach Landing!
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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Other property types in Chatham

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

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

9.6 out of 10, Exceptional, (89)
"Beautiful home! Check in was easy. I had a quick question and the host answered very promptly and was super nice ! House was very clean and the electric fireplace was a plus! We will definitely stay here again! "
The price is AED 415
AED 1,659 total
includes taxes & fees
16 Apr - 17 Apr
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
On the beach, sun loungers

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

10.0 out of 10, Exceptional, (156)
"Our second year visiting and just wonderful! Hope we can always make this our fall getaway!!"
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Edgewater Beach Resort, a VRI resort
BBQ/picnic area

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (261)
"It's a nice property with great views. There are no indoor passageways to your rooms or to the pool. You have to go outdoors to get to them. It's kind of crazy that we got a kitchen area but they didn't have any solder pepper. It was well stocked with everything else to be able to cook but no seasonings. Everything else was wonderful. The beds were comfortable. Housekeeping kept us in towels."
Edgewater Beach Resort, a VRI resort
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.