Holiday Homes in West Chatham

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Featured Holiday Homes in West Chatham

Charming Home Close to Everything. Discounts for the fall and winter

10.0 out of 10, Exceptional, (191)
"This is a well appointed, comfortable property with lots of amenities in a great area. Well stocked kitchen. Host is easy to communicate with and provides good information in the house. "
Charming Home Close to Everything. Discounts for the fall and winter

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

8.0 out of 10, Very good, (63)
"Awesome view very quiet inside could use some refurbishment "
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Idyllic Waterfront Home on Drummer Cove in Quiet Pine Grove on Pleasant Point.

10.0 out of 10, Exceptional, (71)
"This house was really a hidden gem. We enjoyed our stay watching the tide going in and out and seeing the sun rise from the deck while enjoying our morning coffee. The kitchen and bathroom looked newly renovated and the kitchen well equipped. Great location to Marconi Beach, the ponds, Wellfleet Ctr. and Provincetown. Look forward to staying there again! "
Idyllic Waterfront Home on Drummer Cove in Quiet Pine Grove on Pleasant Point.

Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!

9.6 out of 10, Exceptional, (15)
"A group of friends and I had a lovely long weekend stay here. The yard is so big and perfect for games and relaxing, and the house is close to several beaches, mini golf, restaurants, ice cream, etc. The layout is kind of weird, but we had plenty of space for everything. Would stay here again!"
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

10.0 out of 10, Exceptional, (1)
"This property was exactly as described and depicted in the photos. Clean, spacious, and updated. Highly recommend for a stay in Cape Cod. "
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

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

9.6 out of 10, Exceptional, (86)
"Wonderful, restful time in this nice, clean home. "
The price is AU$647
includes taxes & fees
1 Dec - 2 Dec
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Darling Cape Cottage - Steps from Downtown Harwich Port

10.0 out of 10, Exceptional, (51)
"Immaculate home with Cape Cod charm! Fabulous location. Excellent communication with Michael. Quick response to questions. Would absolutely stay again."
Darling Cape Cottage - Steps from Downtown Harwich Port

East Orleans - walk to Nauset Beach

10.0 out of 10, Exceptional, (71)
"Very comfortable home, great location. We look forward to staying here again."
East Orleans - walk to Nauset Beach

Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

9.8 out of 10, Exceptional, (144)
"The house was very nice and the perfect layout for our gang. The check out pricess briught some grumbles from some family membersas well as the 10 AM check out. I explained its a lot of house to clean before a new group at 4PM. A relative that lives on the Cape said the other side of Sea Street is a bit shady, which is why I gave the 4 star for location. "
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

Cape Charmer | Walk to Market, Golf & Eateries | New Kitchen & Big Backyard

9.4 out of 10, Exceptional, (47)
"Quite little home in a private neighborhood. DOG FRIENDLY! We brought our dog to CC for the first time and this property was welcoming of him. Great backyard for kids and lots of games for them as well! "
Cape Charmer | Walk to Market, Golf & Eateries | New Kitchen & Big Backyard

Cozy Cape home with outdoor shower and deck - minutes to beach

9.8 out of 10, Exceptional, (60)
"House was perfect. Wonderful location. Enjoyed stay so much."
Cozy Cape home with outdoor shower and deck - minutes to beach

Ocean Views From Every Room, Beach 30 Seconds Away!

10.0 out of 10, Exceptional, (100)
"This was an unusual situation in that we were getting together to honor and remember three immediate family members we'd lost over the past four years. Cape Cod has always been a special place to us, Hyannis in particular. So there was a lot of pressure as the location could make or break the experience. In making the arrangements I assumed the description of the property had to be slightly exaggerated but the pictures were beautiful, it was pet friendly, and the reviews were all very positive....
Ocean Views From Every Room, Beach 30 Seconds Away!

Relaxing Retreat with Firepit & Outdoor Shower - Near Atlantic & Cape Cod Bay

8.8 out of 10, Excellent, (64)
"We truly enjoyed our time at the Cape. The house was clean, nicely decorated and well equipped with new kitchen appliances. In a nice neighborhood. Only a few issues. Clothes dryer did not work. Upstairs toilet flushing mechanism was tricky. And downstairs dehumidifier had no instructions and would have overflowed had we not discovered that it drained into a closet. We tried reached out to manager and owner but heard nothing. But those things didn’t affect our trip much. Just caused some...
Relaxing Retreat with Firepit & Outdoor Shower - Near Atlantic & Cape Cod Bay

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

10.0 out of 10, Exceptional, (141)
"My husband, dogs, and I stayed for a long weekend in Oct 2024 so we could do hiking trips with out a long commute from our home on upper Cape. It was an ideal location to go to Race Point Beach, Nauset Beach, and Chatham. The property was immaculate, pictures shown absolutely represent the charm of the property. Lots of little extras like a bag of dog treats, bottles of water, kcups, etc. They even had towels & blankets for dogs. Bathrobes to use the jacuzzi. We used the jacuzzi out last...
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub

Petite beach home overlooking Follins Pond w/ central A/C and private gas grill

8.6 out of 10, Excellent, (11)
"We liked the privacy of this small house near the pond (it may not be the best for swimming, but perfect for kayaking and for the views). Outdoor shower, the kayak, clean comfortable bedding, and Vacasa's responsiveness to our questions were high positives. The interior is rather very outdated, but if you expect a cabin - not a luxurious mansion, you won't be disappointed "
Petite beach home overlooking Follins Pond w/ central A/C and private gas grill

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

Cape home with fenced backyard, grill & AC - short walk to beach

8.6 out of 10, Excellent, (26)
"It wad only 5 days and 4 nught..but even tho the house was cleaned and emptied by 2 we vould not enter because it was too early...and yet we had to be out by 10am on our ladt day..so really only had 3 days at cottage though charged for 5..the shades are not blavk our so youre up at 5am..and onlt the upper part of the beach umbrella was there"
Cape home with fenced backyard, grill & AC - short walk to beach

Welcoming home with deck, enclosed yard, outdoor shower, and washer/dryer

9.8 out of 10, Exceptional, (12)
"Loved the spacious fenced in yard and firepit, comfy cozy rooms and furniture, great location, and storage space."
Welcoming home with deck, enclosed yard, outdoor shower, and washer/dryer

Family friendly home, walk to beach, central AC

9.8 out of 10, Exceptional, (8)
"Susan, the owner, is wonderful and responsive Thank you for the stay!"
Family friendly home, walk to beach, central AC

Dreamy Duplex Near Beach with Spacious Patio, Grill, & Outdoor Shower

9.6 out of 10, Exceptional, (37)
"Right next to the beach, which is handy if you plan to walk to the beach and dislike Orleans lack of sidewalks — downside is traffic in front of the property. The property itself is small and very compact. We reserved it for more people than actually ended up coming, so one bathroom and very confined dining space didn’t matter all that muc."
Dreamy Duplex Near Beach with Spacious Patio, Grill, & Outdoor Shower
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 West Chatham

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (254)
"We loved our stay! The 1 bedroom was very clean fully equipped with everything we needed. All the extras like soap for dishes , dishwasher towels for the pool. Pool area very clean beautiful grounds. Friendly staff. "
Edgewater Beach Resort, a VRI resort

The Cove At Yarmouth

3.0 star property
9.2 out of 10, Wonderful, (216)
"I used to be an owner here since it is also a time share, it is like my second home "
The price is AU$244
includes taxes & fees
2 Dec - 3 Dec
The Cove At Yarmouth

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (294)
"The COVE never disappoints. "
The price is AU$218
includes taxes & fees
2 Dec - 3 Dec
The Cove at Yarmouth by VRI Americas
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.