
Guest house holiday rentals in Dennis
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Dennis
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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.

Bright & Cozy with Patio, Grill near Beach & Golf
Peaceful and spacious guesthouse in Brewster - minutes from Wequassett Resort, beaches, golfing & more. This space is complete with cathedral ceilings, skylights, a shared large patio with outdoor seating, gas grill, parking, and a washer/dryer. Enjoy your morning coffee on the patio, Keurig & K-cups provided. Linens, shower essentials, towels, and beach accessories are all supplied. An ideal location & space for a couple's escape with activities, restaurants & shopping moments away!

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.

Questover…steps to the ocean
Private oasis yet steps to the warm and gentle ocean waters of Nantucket Sound..Fresh and modern first floor cottage ..every amenity from new luxe linens..towels..wagon for beach chairs..and children …central air/heat..all on one floor l with lots of light and ocean breezes…outside dining and lounge area…firepit and large cedar outdoor shower…walk to great restaurants, beaches, Pirate museum ..A very special place🌊💫

“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 guest house rentals in Dennis
Family-friendly guest house rentals

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

Queen canopy

Rugosa Guest House - Room 4

Private entrance studio

Rugosa Guest House - Room 3
Guest house rentals with a patio

Mady on the Forest...

Waterfront Cottage / Your Cape Escape

Carriage house in historic district,walk to beach!

West Falmouth treehouse

Charming Cottage in East Dennis

the Elevated Escape

Beach glamping at the Zen Den

Brand new, on a secret pond
Guest house rentals with a washing machine and dryer

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

Private 1 king bedroom guest house-2021 built

Cozy, renovated home in a charming duplex cottage

Cape Cod Cottage: Walk to the Beach in Brewster!

“My Two Buoys” (Side B) Sleeps 6 / Walk to Beaches

Charming Private House all points Cape Cod!

Osterville Guest House

Carriage House - Oyster Pond, Steps to Beach+Town
Quick stats about guest house rentals in Dennis

Total holiday rentals
Explore 10 holiday rentals in Dennis

Nightly prices starting at
Dennis holiday rentals start at $91 SGD per night before taxes and fees

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

Wifi availability
10 of Dennis holiday rentals include wifi 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
- 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
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Fitness-friendly rentals Dennis
- Bed and breakfasts Dennis
- Pet-friendly rentals Dennis
- Family-friendly rentals Dennis
- Waterfront rentals Dennis
- Private suite rentals Dennis
- Rentals with lake access Dennis
- Boutique hotels Dennis
- Rentals with breakfast Dennis
- Rentals with outdoor seating Dennis
- Rentals with a firepit Dennis
- House rentals Dennis
- Rentals with an EV charger Dennis
- Villa rentals Dennis
- Flat rentals Dennis
- Apartment rentals Dennis
- Cottage rentals Dennis
- Rentals with a fireplace Dennis
- Rentals with a hot tub Dennis
- Hotel rooms Dennis
- Rentals with a washing machine and dryer Dennis
- Rentals with a patio Dennis
- Rentals with pools Dennis
- Rentals with beach access Dennis
- Rentals with a kayak Dennis
- Beachfront rentals Dennis
- Guest house rentals Barnstable County
- Guest house rentals Massachusetts
- Guest house rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- White Horse Beach
- Horseneck Beach State Reservation
- Coast Guard Beach
- Pinehills Golf Club
- Chapin Memorial Beach
- Inman Road Beach
- Nauset Beach
- Lighthouse Beach
- Minot Beach
- Town Neck Beach
- Ellis Landing Beach
- Linnell Landing Beach
- New Silver Beach
- Peggotty
- Nickerson State Park
- Falmouth Beach
- Cape Cod Inflatable Park




