
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.

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!

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!

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.

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.

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.

Romantic getaway in historic Barnstable village.
Private bath, entrance and parking. Walk to village, coffee shops, restaurants and harbor for Whale Watching Trips. Short drive to beaches, mall, the town of Hyannis, and ferries to Nantucket and Marthas Vineyard. Close to running, and walking trails. Two night minimum on weekends, three on holiday weekends. Check in at 12.00 noon, check out at 11.00 am.
Popular amenities for Dennis guesthouse rentals
Family-friendly guest house rentals

West Chop Cottage + Beach Access

Cabin @ Newcomb Hollow Beach

#6 Queen bed, location location location

Yarmouth summer rental vacation

Abundant Blessings Cottage – Wellfleet

Queen canopy

Crystal lake getaway

Rugosa Guest House -Room 6 Suite
Guest house rentals with a patio

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

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!

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 guesthouse rentals in Dennis

Total vacation rentals
Explore 10 vacation rentals in Dennis

Nightly prices starting at
Dennis vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 1,630 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
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- The Hamptons Vacation rentals
- Rentals with lake access Dennis
- Boutique hotels Dennis
- Rentals with breakfast Dennis
- Rentals with pools Dennis
- Villa rentals Dennis
- Rentals with a fire pit Dennis
- Rentals with a kayak Dennis
- Apartment rentals Dennis
- Pet-friendly rentals Dennis
- Bed and breakfasts Dennis
- Rentals with an EV charger Dennis
- Rentals with outdoor seating Dennis
- Beachfront rentals Dennis
- Hotel rooms Dennis
- Rentals with beach access Dennis
- Cottage rentals Dennis
- Rentals with a hot tub Dennis
- Rentals with a patio Dennis
- Private suite rentals Dennis
- Condo rentals Dennis
- Family-friendly rentals Dennis
- Waterfront rentals Dennis
- Rentals with a washer and dryer Dennis
- House rentals Dennis
- Rentals with a fireplace Dennis
- Guesthouse rentals Barnstable County
- Guesthouse rentals Massachusetts
- Guesthouse rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- East Sandwich Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- New Silver Beach
- Pinehills Golf Club
- Sandy Neck Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Lighthouse Beach
- Cape Cod Inflatable Park
- Popponesset Peninsula
- Saquish Beach
- Race Point Beach
- Nauset Beach
- Skaket Beach
- Sea Gull Beach
- Scusset Beach State Reservation
- Marconi Beach
- Sandwich Glass Museum




