
Guesthouse vacation rentals in Dennis
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Top-rated guesthouse rentals in Dennis
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Modern Fireplaced Carriage House with Beach Permit
Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

Quaint Cape Cod Cottage
Quaint cottage on Cape Cod, perfect for a last minute getaway. Amazing location with the beach, Shining Sea Bike Path, The Knob, and Spohr Gardens all within WALKING DISTANCE! A five minute drive to Falmouth Main Street which offers amazing restaurants and shops. In the other direction, another five minute drive will bring you to the historical seaside village of Woods Hole, home to world renowned scientists, numerous beaches, restaurants, museums, an aquarium and the Martha's Vineyard Ferry.

Claw Foot Tub & King Bed at Club Tanuki Cottage
Glorious gardens and bay breezes! King-sized Casper bed in romantic antique Cape Cod studio cottage with private entrance & patio, in-room double-slipper claw foot tub, luxe bath amenities, Brooklinen sheets. Just renovated soup-to-nuts! Marble & antique wooden floors, decorated with rotating collection of antiques, original local art & great light. Nestled along historic route 6A (Main Street) near other galleries, museums, walking trails, ponds and beaches; 90 seconds to closest beach.

Charming Antique Cape Cod Cottage
Our cottage is situated in a lovely, landscaped yard with a private deck and back yard for our guests. We have a self check in that allows for privacy. While there is a feeling of privacy, you are close to stores and other conveniences. There are many walking trails nearby and beaches for outdoor activities. Perfect location for getting away or seeking adventure. Be sure to check out our fall and holiday specials. OCTOBER, NOVEMBER AND DECEMBER - BOOK 3 NIGHTS GET FOURTH NIGHT FREE!

Rustic Carriage House by the Sea
This authentic small old Cape Cod rustic carriage house is charming, antique, and unique. It is situated in a beautiful,-of-a-kind location, loaded with cozy fun, making a great getaway time of the year. The carriage house is within distance of beautiful Hens Cove and is near many activities such as bike paths the cape cod canal, ferries, hiking fishing, and numerous restaurants. It is ideal for pet-friendly families, a couple of couples, friends who want to stay together, and larger groups.

Charming Pond-Front Boathouse
Charming antique boat house located directly on Long Pond. Quiet, peaceful accommodations with 180 views. Watch the American Bald Eagles and Osprey search for fish at dusk from your private deck that reaches out over the pond. Long Pond is full recreation, two kayaks and a canoe are available. Hiking, bicycling, golfing, fishing, swimming, boating, snorkeling, sunbathing, and napping are just a few of the activities that can be enjoyed in the quaint, semi-private, pond-front accommodation.

Abundant Blessings Cottage – Wellfleet
Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.

Secluded home for Cape Cod relaxation, exploration
Explore the Cape from this private 1-bedroom, 1-bathroom modern apartment in Bourne. The vacation rental comfortably sleeps 4 and comes with all the conveniences to make your stay on the Cape enjoyable, comfortable and private. Just minutes from the Bourne Bridge, this Cape-side apartment provides the ideal location to explore all the that the South Coast, Cape and Islands has to offer. We welcome guests with small pets, total weight limit of 40 pounds (max 2)

One bedroom guest house on beautiful Cape Cod
Second level guest apartment with one bedroom, bathroom, kitchen, large walk-in closet and living room. Just about everything you need to feel at home. There is A/C in the bedroom and the living area is well vented and has a large ceiling fan. Two golf courses are within 3/4 of a mile, public access beach and boat ramp are within 1 mile. You will also find kayaking, bike trails, walking trails and many other Cape Cod amenities just a short drive away.

Relaxing Cottage in Centerville Village
Welcome to my home! The cottage is located in Historic Centerville Village, it's a welcoming, bright and relaxing, studio space; perfect for a couple, or individual, to getaway on Cape Cod. Salt Tide Cottage is a private guesthouse with off-street parking and a serene outdoor space. It sits behind the main house with its own back yard space with hammock. Just a short walk to the ocean, beaches, the library and the general store.

“The Pink Cottage” in Historic South Yarmouth
“The Pink Cottage” is a charming one-bedroom private building nestled into a beautiful historic property in South Yarmouth. Enter through the pergola patio, enjoy a spacious living space with dining and kitchen area. The one-bedroom with large closet is comfortably outfitted with all linen necessities, full bath with stand-up shower. Outdoor shower just off the patio, grill and more! Very quiet and private.

Joe's Beach Hideaway
Beach is at the end of the dead end road! Very Cute romantic cape cottage! Inside: Queen bed, dresser, couch, new kitchen and bath Outside: table and chairs, outdoor shower, beach chairs, umbrella and grill House has wifi, cable and parking for one car!
Popular amenities for Dennis guesthouse rentals
Family-friendly guest house rentals

West Chop Cottage + Beach Access

*NEW* Cape Cod Bungalow

Mady on the Forest...

Oak bluffs cottage Perfect place to honeymoon!

Cozy Apartment Nearby Pond, Beaches, Golf Course.

Sankaty Light Studio Cottage

Carriage House Retreat in the Heart of Hyannis!

Yarmouth summer rental vacation
Guest house rentals with a patio

Private 1 king bedroom guest house-2021 built

Waterfront Cottage / Your Cape Escape

Charming Private House all points Cape Cod!

Carriage House - Oyster Pond, Steps to Beach+Town

the Elevated Escape

Beach glamping at the Zen Den

Cozy Cottage

Newly renovated studio in heart of Marion village
Guest house rentals with a washer and dryer

Harwich Port - "Lee Side" cottage by the beach!

Carriage house with deck. Pondfront. Large lawns.

Cozy, renovated home in a charming duplex cottage

Cape Cod Cottage: Walk to the Beach in Brewster!

Carriage house in historic district,walk to beach!

Osterville Guest House

Brand new, on a secret pond

Cape Cod beach inspired “Makondo” Suit Apartment!
Quick stats about guesthouse rentals in Dennis

Total vacation rentals
Explore 10 vacation rentals in Dennis

Nightly prices starting at
Dennis vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

Verified guest reviews
Over 1,590 verified reviews to help you choose

Wi-Fi availability
10 of Dennis vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Dennis rentals

4.9 Average rating
Dennis stays are highly rated by guests—averaging 4.9 out of 5!
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- Cape Cod
- West Dennis Beach
- East Sandwich Beach
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