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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 3031 Vacation Homes in South Dennis with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (90)
"This was our second time staying at this property and we loved it even more than the first! The location is amazing and the surrounding neighborhoods create the perfect location for both people and pets! "
The price is AED 327
AED 1,641 total
includes taxes & fees
11 May - 12 May
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
Outdoor spa tub

WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

10.0 out of 10, Exceptional, (86)
"Wonderful property!"
The price is AED 1,028
AED 2,497 total
includes taxes & fees
22 May - 23 May
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Sand Bar-Dog Friendly on Cooks Brook Beach
Fridge, microwave, oven, stovetop

Sand Bar-Dog Friendly on Cooks Brook Beach

10.0 out of 10, Exceptional, (15)
"The house was comfortable and proximity to the beach was great. Hosts were attentive and friendly. Thanks for a great stay"
The price is AED 937
AED 2,161 total
includes taxes & fees
13 May - 14 May
Sand Bar-Dog Friendly on Cooks Brook Beach
Cape Cod cottage
Exterior

Cape Cod cottage

9.6 out of 10, Exceptional, (101)
"House was very clean. Nicely decorated. Peaceful. Has everything you may need. Check in and check out was smooth. I even walked in to a nice little surprise. Highly recommend."
Cape Cod cottage
Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach
TV, books

Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

8.0 out of 10, Very Good, (9)
"Easy walk to Great Pond and the Bay."
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
Exterior

OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

10.0 out of 10, Exceptional, (103)
"Fantastic location, right on the beach and convenient to restaurants and shops."
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
Secluded home with firepit, & scenic yard - near Nauset Beach & shops
Exterior

Secluded home with firepit, & scenic yard - near Nauset Beach & shops

8.0 out of 10, Very Good, (38)
"I had a great Labor Day weekend here with my family. The house was very clean and very close to Nauset Light Beach. I would definitely stay here again."
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
Miscellaneous

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 AED 331
AED 1,156 total
includes taxes & fees
11 May - 12 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
Smart TV, fireplace, books

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!
Interior

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.
Outdoor dining

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

10.0 out of 10, Exceptional, (73)
"Impressed with everything. Would stay there again."
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Oldest Town of Cape Cod In The Historic District
Fridge, microwave, oven, stovetop

Oldest Town of Cape Cod In The Historic District

9.4 out of 10, Exceptional, (3)
"The property has a great location and was very well kept up. We were out a lot at a conference but really enjoyed the property and the owner. "
The price is AED 349
AED 1,291 total
includes taxes & fees
8 Jun - 9 Jun
Oldest Town of Cape Cod In The Historic District
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Interior

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

9.6 out of 10, Exceptional, (109)
"Really amazing, breathtaking views, private! A great retreat for family time. "
The price is AED 2,567
AED 4,704 total
includes taxes & fees
11 May - 12 May
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Cozy Yarmouth Cottage
Property grounds

Cozy Yarmouth Cottage

9.6 out of 10, Exceptional, (5)
"Beautiful and comfortable space perfect for our family of four. "
Cozy Yarmouth Cottage
Close to Bike Path 1 Mile to Beaches!
Beach nearby

Close to Bike Path 1 Mile to Beaches!

9.6 out of 10, Exceptional, (16)
"Perfect little get away and quiet and private. SO close to so many attractions."
Close to Bike Path 1 Mile to Beaches!
Pond Perch: 239-B Brewster Pond Front Perfection, Walk to Private Beach
Fridge, microwave, oven, stovetop

Pond Perch: 239-B Brewster Pond Front Perfection, Walk to Private Beach

10.0 out of 10, Exceptional, (5)
"Beautiful setting"
Pond Perch: 239-B Brewster Pond Front Perfection, Walk to Private Beach
Hot Tub, 200 ft to Beach!
Outdoor dining

Hot Tub, 200 ft to Beach!

9.8 out of 10, Exceptional, (8)
"The property was beautiful and the beds were extremely comfortable. The property management was responsive and helpful."
Hot Tub, 200 ft to Beach!
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (147)
"Great place to stay with family and pet."
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
Terrace/patio

Oakwood Trail Cottage | Eastham home on Cape Cod Rail Trail with great deck

8.0 out of 10, Very Good, (5)
"The property was exactly what we were looking for, plenty of space, comfortable beds, a beautifully wooded lot, and right near the bike trail. We had a wonderful breeze through the house."
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
Smart TV, fireplace, DVD player, foosball

Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food

9.8 out of 10, Exceptional, (132)
"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 - Mem Day day weekend or longer is still available.
Sun loungers

Quiet Northside Beach House - Mem Day day weekend or longer is still available.

9.8 out of 10, Exceptional, (27)
"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 - Mem Day day weekend or longer is still available.
The Cove At Yarmouth
Beach nearby

The Cove At Yarmouth

3.0 star property
9.2 out of 10, Wonderful, (236)
"It is a very nice place to stay"
The price is AED 521
AED 596 total
includes taxes & fees
11 May - 12 May
The Cove At Yarmouth
Edgewater Beach Resort, a VRI resort
BBQ/picnic area

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (269)
"I love staying here "
The price is AED 760
AED 870 total
includes taxes & fees
15 May - 16 May
Edgewater Beach Resort, a VRI resort
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.