Guesthouse holiday rentals in Dennis
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Top-rated Guesthouses in Dennis
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Dennis guesthouses
Family-Friendly guesthouses
Guesthouse in Vineyard Haven
4.94 out of 5 average rating, 126 reviewsWest Chop Cottage + Beach Access
Guesthouse in Wellfleet
5 out of 5 average rating, 18 reviewsPeaceful, Family-Friendly Cottage, w/Private Beach
Guesthouse in Dennis Port
4.85 out of 5 average rating, 257 reviewsJoe's Beach Hideaway
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 81 reviewsMermaid Cottage
Guesthouse in Barnstable
4.9 out of 5 average rating, 58 reviewsOsterville Guest House
Guesthouse in Eastham
4.82 out of 5 average rating, 11 reviewsCozy 2 bedroom home near Rock Harbor/ bike trail
Guesthouse in Falmouth
4.72 out of 5 average rating, 68 reviewsCOZY GUESTHOUSE
Guesthouse in Tisbury
4.86 out of 5 average rating, 246 reviewsAdorable Vineyard Haven Cottage
Guesthouses with a patio
Guesthouse in Sandwich
4.97 out of 5 average rating, 62 reviewsPrivate 1 king bedroom guest house-2021 built
Guesthouse in Mashpee
4.92 out of 5 average rating, 26 reviewsMady on the Forest...
Guesthouse in Pocasset
5 out of 5 average rating, 61 reviewsWaterfront Cottage / Your Cape Escape
Guesthouse in West Yarmouth
5 out of 5 average rating, 34 reviewsCozy, renovated home in a charming duplex cottage
Guesthouse in Oak Bluffs
Fantastical Fishermen’s Cottage & private Garden
Guesthouse in Chatham
4.95 out of 5 average rating, 22 reviewsCarriage House - Oyster Pond, Steps to Beach+Town
Guesthouse in Yarmouth
5 out of 5 average rating, 23 reviewsCozy Cottage
Guesthouse in Brewster
4.98 out of 5 average rating, 57 reviewsBrand new, on a swimmable pond
Guest house rentals with a washing machine and dryer
Guesthouse in Harwich Port
4.94 out of 5 average rating, 17 reviewsHarwich Port - "Lee Side" cottage by the beach!
Guesthouse in East Falmouth
4.73 out of 5 average rating, 63 reviewsArtsy Airpark Apartment
Guesthouse in Brewster
4.93 out of 5 average rating, 72 reviewsCape Cod Cottage: Walk to the Beach in Brewster!
Guesthouse in Yarmouth
4.87 out of 5 average rating, 15 reviewsCarriage house in historic district,walk to beach!
Guesthouse in West Tisbury
4.94 out of 5 average rating, 17 reviewsGuest house over Garage
Guesthouse in Tisbury
5 out of 5 average rating, 7 reviewsEscape to Bungalow 24 on MV!
Guesthouse in Brewster
4.89 out of 5 average rating, 45 reviewsCape Cod beach inspired “Makondo” Suit Apartment!
Guesthouse in Yarmouth
5 out of 5 average rating, 14 reviewsPristine Mid Cape Carriage House w/ Ocean Views
Quick stats about guesthouse rentals in Dennis
Total rentals
20 properties
Nightly prices starting at
$174 AUD before taxes and fees
Total number of reviews
1.3K reviews
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
West Dennis Beach, Whydah Pirate Museum and Sesuit Harbor Cafe
Destinations to explore
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