
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.

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!

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.

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.

Wellfleet Oasis
Unwind in this calm, stylish studio oasis. Stroll to Mass Audubon or bike just 1.3 miles along the trail next to our development to reach Marconi Beach. Enjoy local restaurants, a flea market, and Wellfleet Drive just 0.9 miles away. A small market on the Eastham-Wellfleet line offers essentials, sandwiches, and drinks. With owners on-site, the space features a private entrance, a deck with an electric grill, and an outdoor solar shower for rinsing off after a sunny day.

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.

Charming & quiet 1 bedroom apartment
Located above an oversized garage - this newly constructed 1 bedroom/1 bathroom apartment will be your home away from home. With air conditioning and super fast wi-fi you will be quite comfortable. This apartment sits up in the canopy of trees that surround our property. Our back yard gives you immediate access to 60 acres of open space with trails
Popular amenities for Dennis guesthouse rentals
Family-friendly guest house rentals

Rugosa Guest House - Room 4

Peaceful, Family-Friendly Cottage, w/Private Beach

Stylish Artist Cottage Near Beach &Plimoth Patuxet

Queen canopy

Rugosa Guest House - Room 8, Captain's Quarters

Rugosa Guest House - Room 7 Suite
Guest house rentals with a patio

*NEW* Cape Cod Bungalow

Waterfront Cottage / Your Cape Escape

Carriage House Retreat in the Heart of Hyannis!

West Falmouth treehouse

Claw Foot Tub & King Bed at Club Tanuki Cottage

Charming Cottage in East Dennis

the Elevated Escape

Beach glamping at the Zen Den
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!

Carriage house in historic district,walk to beach!

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

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!
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- Cape Cod
- Mayflower Beach
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- Craigville Beach
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- Pinehills Golf Club
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