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

Nautical loft guest house with hot tub and sauna
Keep it simple at this peaceful and centrally-located space. Walking distance to several downtown shops and restaurants, and only one mile from the beach, this loft boasts skylights, cedar hot tub and sauna, outdoor shower and full kitchen. If you are traveling through Sandwich, this loft is a must-see. We recommend this space for two people. While you can technically fit 4, it is quite crowded. If you plan to use the hot tub or sauna, please let us know in advance so we can set it up for you.

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.

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.

Brand new, on a secret pond
Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

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.

MV King bed, Water Views, Near Bike Path- Bus stop
Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay. :)

Cottage in Centerville (BEACH PASS)
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

1-Bedroom seasonal cottage near National Seashore

Wedding RetreatTrails Golfing Beaches Private Gem

Charming W. Tisbury Studio Guest Cottage

Adorable 1-bed guest house, walk to beach

Marthas Vineyard 1BR Cottage 10 min to beach/town

Pet-Friendly Edgartown Home | 2BR Near Trails

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

Charming seaside cottage ocean view
Guest house rentals with a patio

Private cabin in Wildlife Habitat; near bus route

Waterfront Cottage / Your Cape Escape

Carriage house in historic district,walk to beach!

Charming Private House all points Cape Cod!

Claw Foot Tub & King Bed at Club Tanuki Cottage

the Elevated Escape

Beach glamping at the Zen Den

Cozy Cottage
Guest house rentals with a washer and dryer

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

Private 1 king bedroom guest house-2021 built

Cozy, vacation home in a charming duplex cottage

Cape Cod Cottage: Walk to the Beach in Brewster!

Osterville Guest House

Carriage House - Oyster Pond, Steps to Beach+Town

Spacious Guest House in Falmouth Village

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 G$12,547 GYD per night before taxes and fees

Verified guest reviews
Over 1,650 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!
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Newark Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Providence Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- York County Vacation rentals
- Cambridge Vacation rentals
- Bar Harbor Vacation rentals
- Rentals with a kayak Dennis
- Rentals with a hot tub Dennis
- Fitness-friendly rentals Dennis
- Apartment rentals Dennis
- Pet-friendly rentals Dennis
- Bed and breakfasts Dennis
- House rentals Dennis
- Rentals with outdoor seating Dennis
- Boutique hotels Dennis
- Rentals with breakfast Dennis
- Private suite rentals Dennis
- Rentals with a washer and dryer Dennis
- Villa rentals Dennis
- Rentals with a patio Dennis
- Rentals with an EV charger Dennis
- Rentals with pools Dennis
- Rentals with lake access Dennis
- Cottage rentals Dennis
- Beachfront rentals Dennis
- Hotel rooms Dennis
- Rentals with beach access Dennis
- Rentals with a fire pit Dennis
- Family-friendly rentals Dennis
- Waterfront rentals Dennis
- Rentals with a fireplace Dennis
- Condo rentals Dennis
- Guesthouse rentals Barnstable County
- Guesthouse rentals Massachusetts
- Guesthouse rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Pinehills Golf Club
- Sandy Neck Beach
- New Silver Beach
- Coast Guard Beach
- Nauset Beach
- Falmouth Heights Beach
- Skaket Beach
- Saquish Beach
- Race Point Beach
- Cape Cod Inflatable Park
- Nickerson State Park
- Lighthouse Beach
- Cahoon Hollow Beach
- Popponesset Peninsula
- Cape Cod Canal
- Sea Gull Beach
- Inkwell Beach





