East Dennis Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for East Dennis vacation rentals

Terrace/patio
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Cottage in Chatham

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is ￥13,555
￥50,873 total
includes taxes & fees
Dec 17 - Dec 18
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
TV, fireplace, books
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Vacation Home in Chatham

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
9.6 out of 10, Exceptional, (101)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is ￥15,269
￥65,144 total
includes taxes & fees
Dec 17 - Dec 18
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Smart TV, books
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Vacation Home in West Brewster

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
The price is ￥19,998
￥107,770 total
includes taxes & fees
Dec 17 - Dec 18
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Outdoor dining
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Cottage in Eastham

🦀Waterfront at The Velvet Crab~Amazing Sunsets
9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is ￥24,398
￥66,978 total
includes taxes & fees
Dec 17 - Dec 18
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Property grounds
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Vacation Home in Dennis

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
The price is ￥21,658
￥52,452 total
includes taxes & fees
Dec 17 - Dec 18
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Indoor pool, seasonal outdoor pool
The Cove at Yarmouth by Westgate Resorts

Aparthotel in West Yarmouth

The Cove at Yarmouth by Westgate Resorts
3.0 star property
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is ￥18,267
￥20,907 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Cove at Yarmouth by Westgate Resorts
Outdoor dining
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Vacation Home in Wellfleet

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
10.0 out of 10, Exceptional, (75)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is ￥21,735
￥67,496 total
includes taxes & fees
Dec 17 - Dec 18
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Pool
Cozy Large Home in Harwich with Patio near Wequassett Resort

Vacation Home in Harwich

Cozy Large Home in Harwich with Patio near Wequassett Resort
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is ￥24,774
￥80,926 total
includes taxes & fees
Dec 19 - Dec 20
Cozy Large Home in Harwich with Patio near Wequassett Resort
Beach nearby
Quaint condo near private beach access with fireplace - close to dining

Condo in Dennis Port

Quaint condo near private beach access with fireplace - close to dining
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is ￥10,439
￥49,750 total
includes taxes & fees
Dec 18 - Dec 19
Quaint condo near private beach access with fireplace - close to dining
Outdoor dining
Sleeps 2-8/Soaking Tub/FirePit~Burrows

Vacation Home in Eastham

Sleeps 2-8/Soaking Tub/FirePit~Burrows
10.0 out of 10, Exceptional, (7)
"Overall, we had a really great stay. The home is in a quiet neighborhood & close to the beach. Everything was clean and as described in the listing. "
United States
Kallee M.
The price is ￥24,227
￥78,729 total
includes taxes & fees
Dec 17 - Dec 18
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Smart TV, fireplace
The Pet-Friendly Surf Shack Hideaway on the Cove

Vacation Home in Eastham

The Pet-Friendly Surf Shack Hideaway on the Cove
10.0 out of 10, Exceptional, (21)
"Lovely property, spacious and VERY clean..location is ideal..."
United States
Kathy M.
The price is ￥25,251
￥78,117 total
includes taxes & fees
Dec 17 - Dec 18
The Pet-Friendly Surf Shack Hideaway on the Cove
Smart TV, fireplace
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Vacation Home in Eastham

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
9.6 out of 10, Exceptional, (4)
"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"
United States
Kim S.
The price is ￥24,398
￥78,925 total
includes taxes & fees
Dec 17 - Dec 18
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Dining
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Vacation Home in Orleans

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
10.0 out of 10, Exceptional, (14)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
United States
Darren Y.
The price is ￥280,458
￥488,788 total
includes taxes & fees
Dec 17 - Dec 18
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Outdoor dining
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Vacation Home in West Brewster

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is ￥22,281
￥82,974 total
includes taxes & fees
Dec 17 - Dec 18
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Interior
Pond House~Waterfront Oasis W/Jacuzzi Tub

Vacation Home in Eastham

Pond House~Waterfront Oasis W/Jacuzzi Tub
10.0 out of 10, Exceptional, (10)
"Beautiful spot ! House was clean and well equipped. "
United States
Cynthia P.
The price is ￥24,398
￥78,925 total
includes taxes & fees
Dec 17 - Dec 18
Pond House~Waterfront Oasis W/Jacuzzi Tub
Indoor spa tub
Brewster Green Resort

Aparthotel in Brewster

Brewster Green Resort
3.5 star property
9.4 out of 10, Exceptional, (121)
"Super clean and a really large space! "
United States
Linda
The price is ￥26,197
￥29,982 total
includes taxes & fees
Dec 19 - Dec 20
Brewster Green Resort
Beach nearby
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Vacation Home in Barnstable

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is ￥23,216
￥80,925 total
includes taxes & fees
Dec 17 - Dec 18
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Property grounds
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Apartment in Eastham

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
10.0 out of 10, Exceptional, (18)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is ￥31,905
￥80,561 total
includes taxes & fees
Dec 29 - Dec 30
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Beach nearby
Charming House by the Beach with Patio, Grill, FirePit

Vacation Home in Bass River

Charming House by the Beach with Patio, Grill, FirePit
9.8 out of 10, Exceptional, (7)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
The price is ￥31,006
￥93,875 total
includes taxes & fees
Dec 17 - Dec 18
Charming House by the Beach with Patio, Grill, FirePit
Interior
The Nantucket Room Unit - #2

Condo in Harwich port

The Nantucket Room Unit - #2
9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is ￥19,476
￥34,960 total
includes taxes & fees
Dec 17 - Dec 18
The Nantucket Room Unit - #2
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 East Dennis Hotel Reviews

Chatham Bars Inn

Chatham Bars Inn

10/10 Excellent
"Helpful staff & food & drinks were great ! "
glen 1-night trip
Posted 4 days ago
Chatham Bars Inn

Find out more about East Dennis

Search for holiday rentals in East Dennis on Expedia! You can easily find your home rentals, villas, holiday apartments in East Dennis using one of the methods below:

  • View our selection of featured holiday rentals in East Dennis
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Look no further and take a look at our great range of rental properties in East Dennis!

Frequently asked questions

Are there vacation rentals in East Dennis?

Yes, we offer vacation rentals in East Dennis close to Eden Hand Arts, or you can select a more remote option if you're looking for extra privacy while you relax. East Dennis is known for its beaches.

What's the top vacation rental that East Dennis has to offer?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: Visitors like this East Dennis vacation home rental. It is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in East Dennis?

Choose from 56 Expedia vacation rentals in East Dennis for a memorable vacation.

What’s there to see and do in East Dennis?

Corporation Beach and Cape Cod Beaches are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Eden Hand Arts. Crowe's Pasture and Cape Playhouse are a couple of places you'll find in the larger area.

What’s a vacation rental in East Dennis like?

Vacation rentals are privately owned properties where you can stay for a couple of days or more in East Dennis. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.