East Dennis Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for East Dennis holiday rentals

Fridge, microwave, oven, stovetop
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 HK$708
HK$2,604 total
includes taxes & fees
7 Jan - 8 Jan 2026
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Exterior
Cozy Large Home in Harwich with Patio near Wequassett Resort

Holiday 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 HK$1,237
HK$4,022 total
includes taxes & fees
16 Jan - 17 Jan 2026
Cozy Large Home in Harwich with Patio near Wequassett Resort
Fridge, microwave, oven, stovetop
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Holiday 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 HK$1,150
HK$5,571 total
includes taxes & fees
27 Dec - 28 Dec
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 HK$1,209
HK$3,324 total
includes taxes & fees
7 Jan - 8 Jan 2026
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Microwave, oven, stovetop, dishwasher
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Holiday Home in Chatham

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
9.6 out of 10, Exceptional, (102)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is HK$887
HK$3,386 total
includes taxes & fees
6 Jan - 7 Jan 2026
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Beach
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Holiday 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 traveller
The price is HK$1,159
HK$2,713 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Marina
Lovely House 5 Min to Beach with Deck, Grill, Garage

Holiday Home in Eastham

Lovely House 5 Min to Beach with Deck, Grill, Garage
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is HK$1,081
HK$3,686 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lovely House 5 Min to Beach with Deck, Grill, Garage
Outdoor dining
Sleeps 2-8/Soaking Tub/FirePit~Burrows

Holiday 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 HK$1,209
HK$3,948 total
includes taxes & fees
28 Dec - 29 Dec
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Pool
Stylish 2nd floor Ocean Edge condo

Apartment in Brewster

Stylish 2nd floor Ocean Edge condo
9.8 out of 10, Exceptional, (9)
"Great property. It looks like it was recently renovated and done really well. Convenient to the beaches and restaurants, and golf. We love Brewster. "
United States
Garret J.
The price is HK$1,384
HK$3,329 total
includes taxes & fees
30 Dec - 31 Dec
Stylish 2nd floor Ocean Edge condo
Outdoor dining
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Holiday 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 HK$1,085
HK$3,360 total
includes taxes & fees
7 Jan - 8 Jan 2026
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Exterior detail
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 HK$972
HK$1,745 total
includes taxes & fees
29 Dec - 30 Dec
The Nantucket Room Unit - #2
Outdoor dining
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Holiday Home in Dennis

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
The price is HK$693
HK$2,431 total
includes taxes & fees
28 Dec - 29 Dec
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Smart TV, fireplace
The Pet-Friendly Surf Shack Hideaway on the Cove

Holiday 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 HK$1,252
HK$3,881 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Pet-Friendly Surf Shack Hideaway on the Cove
Fridge, microwave, oven, stovetop
Sand Bar-Dog Friendly on Cooks Brook Beach

Holiday Home in Eastham

Sand Bar-Dog Friendly on Cooks Brook Beach
10.0 out of 10, Exceptional, (23)
"Lovely time!"
United States
Joan W.
The price is HK$1,355
HK$3,723 total
includes taxes & fees
5 Jan - 6 Jan 2026
Sand Bar-Dog Friendly on Cooks Brook Beach
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 HK$1,490
HK$3,895 total
includes taxes & fees
29 Dec - 30 Dec
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Fridge, microwave, oven, stovetop
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Holiday 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 HK$1,198
HK$4,290 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Interior
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

Cottage in Dennis

Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
9.6 out of 10, Exceptional, (177)
"Fenced in yard was perfect and close walk to both beach and restaurants."
United States
Mike Kayla B.
The price is HK$1,478
HK$2,724 total
includes taxes & fees
26 Dec - 27 Dec
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
Interior
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Holiday 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 HK$1,218
HK$3,940 total
includes taxes & fees
29 Dec - 30 Dec
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Interior
National Seashore/Updated/Game Room~Blue Pearl

Holiday Home in Eastham

National Seashore/Updated/Game Room~Blue Pearl
10.0 out of 10, Exceptional, (8)
"Best rental we have stayed in on Cape, and we go every year. Exceptionally clean, comfortable. I can not say enough about it. Great location as well. What stood out the most was the high quality linens, as well as comfortable mattresses. It is very well kept with attention to detail. The grill and appliances were also of a higher quality and made it a pleasure to cook. Will absolutely stay at Blue Pearl again. "
United States
Nicole V.
The price is HK$1,209
HK$3,823 total
includes taxes & fees
7 Jan - 8 Jan 2026
National Seashore/Updated/Game Room~Blue Pearl
4 bedrooms, desk, free WiFi, bed sheets
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Holiday Home in Eastham

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
10.0 out of 10, Exceptional, (2)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
The price is HK$1,490
HK$5,106 total
includes taxes & fees
7 Jan - 8 Jan 2026
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
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 Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Charming, cozy , clean! "
Erica 1-night trip
Posted 4 days ago
Chatham Wayside 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
  • Use the map to find apartments and other holiday homes in the East Dennis neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in East Dennis while they last

Look no further and take a look at our great range of rental properties in East Dennis!

Frequently asked questions

Are there holiday rentals in East Dennis?

Yes, there are holiday rentals in East Dennis close to Eden Hand Arts, or you can select a more secluded option if you're looking for a relaxing stay. East Dennis is known for its beaches.

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

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This holiday home rental outside of East Dennis is located in the city centre, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in East Dennis?

Choose from 57 Expedia holiday rentals in East Dennis for a memorable holiday.

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 wider area.

What’s a holiday rental in East Dennis like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in East Dennis. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.