South 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 South Dennis holiday rentals

Interior
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is HK$1,159
HK$3,736 total
includes taxes & fees
7 Jan - 8 Jan 2026
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Property grounds
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
Dennis
8.8 out of 10, Excellent, (8)
"Five star because hosts were very responsive and truly went out of their way to make sure our stay was comfortable and enjoyable. Mid cape location is perfect for all the beaches we visit and biking we do. "
United States
Mark L.
The price is HK$1,402
HK$4,248 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
Private beach nearby, beach bar
The Club at New Seabury

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (340)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury
Fridge, microwave, oven, stovetop
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

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

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Chatham
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
Fridge, microwave, oven, stovetop
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
West Brewster
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

🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
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
Exterior
Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
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$4,031 total
includes taxes & fees
9 Jan - 10 Jan 2026
Cozy Large Home in Harwich with Patio near Wequassett Resort
Beach
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is HK$1,003
HK$2,524 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Microwave, oven, stovetop, dishwasher
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
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
Outdoor dining
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Wellfleet
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
Outdoor dining
Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
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
Fridge, microwave, oven, stovetop
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
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
Fridge, microwave, oven, stovetop
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
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
Smart TV, fireplace
The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
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
Outdoor dining
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
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
Marina
Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
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
4 bedrooms, desk, free WiFi, bed sheets
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Eastham
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
Interior
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Eastham
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!
Outdoor dining
The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!
Eastham
9.2 out of 10, Wonderful, (11)
"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."
United States
Jennifer G.
The price is HK$1,346
HK$4,104 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Alpine/Walk to Beach for 2 or more!
Fridge, microwave, stovetop, dishwasher
Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining
Dennis Port
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is HK$552
HK$2,530 total
includes taxes & fees
7 Jan - 8 Jan 2026
Quaint condo near private beach access with fireplace - close to dining
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 South 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 South Dennis

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

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

Frequently asked questions

Can I find holiday rentals in South Dennis?

Yes, there are holiday rentals close to the most popular sights in South Dennis, or you can select a more secluded option if you're looking for a relaxing stay.

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

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This holiday home rental outside of South 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 will I find in South Dennis?

Choose from 83 Expedia holiday rentals in South Dennis for a memorable holiday.

What can I see and do in South Dennis?

Cape Cod Rail Trail and Cape Cod Beaches are a couple of lovely local spots to get outside and enjoy nature. Crowe's Pasture and Follins Pond are a couple of places you'll find in the wider area.

What’s a holiday rental in South Dennis like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Dennis. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for families.