
Guesthouse holiday rentals in Dennis
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in Dennis
Guests agree: These guesthouses 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.

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.

Cozy studio in Plymouth
Coastal Charm Meets Cozy Comfort – Your Perfect Getaway Awaits! Beautifully designed studio just 3 minutes from the beach just cross the street! Vintage Farmhouse style – Fully renovated space with a well-equipped kitchen, modern bathroom, and cozy bedroom. Peaceful location surrounded by nature. Perfect for relaxing, unwinding, and enjoying the coastal lifestyle. 18 Minutes to downtown, restaurants, and shops — the ultimate coastal retreat!

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 guesthouses
Family-Friendly guesthouses

West Chop Cottage + Beach Access

Peaceful, Family-Friendly Cottage, w/Private Beach

Wellfleet loft-style guest house close to beaches

#6 Queen bed, location location location

Oak bluffs cottage Perfect place to honeymoon!

Queen canopy

Private entrance studio

Rugosa Guest House - Room 3
Guesthouses with a patio

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

Private 1 king bedroom guest house-2021 built

Waterfront Cottage / Your Cape Escape

Cozy, renovated home in a charming duplex cottage

Charming Private House all points Cape Cod!

Carriage House - Oyster Pond, Steps to Beach+Town

the Elevated Escape

Cozy Cottage
Guest house rentals with a washing machine and dryer

Carriage house with deck. Pondfront. Large lawns.

Cape Cod Cottage: Walk to the Beach in Brewster!

Carriage house in historic district,walk to beach!

Osterville Guest House

Newly furnished-Enjoy sun drenched days

Brand new, on a secret pond

Cape Cod beach inspired “Makondo” Suit Apartment!

Pristine Mid Cape Carriage House w/ Ocean Views
Quick stats about guesthouse rentals in Dennis

Total holiday rentals
Explore 10 holiday rentals in Dennis

Nightly prices starting at
Dennis holiday rentals start at $121 NZD per night before taxes and fees

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

Wi-Fi availability
10 of Dennis holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Dennis rentals

4.9 Average rating
Dennis stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with a fire pit Dennis
- Fitness-friendly rentals Dennis
- Private suite rentals Dennis
- Rentals with a patio Dennis
- Boutique hotel rentals Dennis
- Rentals with breakfast Dennis
- Rentals with outdoor seating Dennis
- Apartment rentals Dennis
- Villa rentals Dennis
- Rentals with a kayak Dennis
- Rentals with pools Dennis
- Rentals with a fireplace Dennis
- Bed and breakfasts Dennis
- Rentals with lake access Dennis
- Pet-friendly rentals Dennis
- Hotel rentals Dennis
- Rentals with beach access Dennis
- House rentals Dennis
- Cottage rentals Dennis
- Beach house rentals Dennis
- Family-friendly rentals Dennis
- Waterfront rentals Dennis
- Rentals with a hot tub Dennis
- Condo rentals Dennis
- Rentals with a washing machine and dryer Dennis
- Rentals with an EV charger Dennis
- Beachfront rentals Dennis
- Guesthouse rentals Barnstable County
- Guesthouse rentals Massachusetts
- Guesthouse rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Horseneck Beach State Reservation
- White Horse Beach
- Coast Guard Beach
- Chapin Memorial Beach
- Pinehills Golf Club
- Minot Beach
- Nauset Beach
- Lighthouse Beach
- Inman Road Beach
- Town Neck Beach
- Ellis Landing Beach
- Nickerson State Park
- New Silver Beach
- Falmouth Beach
- Cape Cod Inflatable Park
- Scusset Beach
- Peggotty Beach