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Compare 2997 Vacation Homes in South Dennis with updated reviews, rates, and availability.

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 SAR 387
SAR 1,755 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

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

10.0 out of 10, Exceptional, (15)
"Hope to be back soon!"
The price is SAR 1,151
SAR 2,438 total
includes taxes & fees
8 Apr - 9 Apr
Sand Bar-Dog Friendly on Cooks Brook Beach

Cape Cod cottage

9.6 out of 10, Exceptional, (99)
"It was perfect! Everything we needed! Thank you for the arrival package! "
Cape Cod cottage

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

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

8.0 out of 10, Very Good, (38)
"Location was very convenient to all the beaches and hiking! 4 stars for the location and price compared to other options, but be aware that the amenities are pretty basic. The house was adequately sized for our family of four but teens found the beds very small. (Room w 2 twins is clearly geared towards littles, w kitschy Tinkerbell lamps.) As others mentioned, bathroom repairs are needed (instead of fixing the running toilet, they just removed the flusher entirely, plus we noted a few other...
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

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"
The price is SAR 469
SAR 1,349 total
includes taxes & fees
7 May - 8 May
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

6 Richards Way - New Listing! East Sandwich Home with Hot Tub & Near Beach

6 Richards Way - New Listing! East Sandwich Home with Hot Tub & Near Beach

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.

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.

Oldest Town of Cape Cod In The Historic District

9.0 out of 10, Wonderful, (2)
"The location worked perfectly for us. Thanks, Ed! "
The price is SAR 375
SAR 1,091 total
includes taxes & fees
4 May - 5 May
Oldest Town of Cape Cod In The Historic District

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (109)
"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

9.6 out of 10, Exceptional, (5)
"Beautiful and comfortable space perfect for our family of four. "
The price is SAR 420
SAR 1,031 total
includes taxes & fees
21 Apr - 22 Apr
Cozy Yarmouth Cottage

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

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!

9.8 out of 10, Exceptional, (8)
"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

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

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

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
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 South Dennis

Quiet Northside Beach House -Spring is hear and summer is on its way.

9.8 out of 10, Exceptional, (25)
"The property is amazing! Great room, very clean and centralto everything you can do on the cape. Mr Steinkrauss is also an excellent communicator and made sure to make our family feel as close to home as possible on the cape. 10/10, would stay again and i highly recommend anyone looking for a beautiful spot with that northeastern feel to look very closely at this!"
Quiet Northside Beach House -Spring is hear and summer is on its way.

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (265)
"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

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (315)
"accommodation was good but cleanliness could have been better. Not bad but some areas needed more attention. Good restaurant and bar service on Thursday. No restaurant available on Saturday."
The price is SAR 757
SAR 866 total
includes taxes & fees
29 Apr - 30 Apr
The Club at New Seabury
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.