Guesthouse vacation rentals in Dennis

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Top-rated guesthouse rentals in Dennis

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Guest favorite

Guesthouse in Centerville

5 out of 5 average rating, 132 reviews

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.

Guest favorite

Guesthouse in Woods Hole

4.89 out of 5 average rating, 174 reviews

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.

Guest favorite

Guesthouse in Wareham

4.96 out of 5 average rating, 103 reviews

Behind Home Plate

Welcome to Behind Home Plate. Summer home to a Cape Cod Baseball League future major leaguer. This studio cottage is located in Indian Mound Beach community with a bay beach at the end of the street. Bring your bikes because the Cape Cod Canal and Onset Village are only minutes away. Easy access to Plymouth, Cape Cod, Boston and Providence. Golf is only minutes from here along with many great restaurants. What a great place to make home base while you explore this area with so much to enjoy.

Guest favorite

Guesthouse in Plymouth

4.93 out of 5 average rating, 122 reviews

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.

Guest favorite

Guesthouse in Wellfleet

4.97 out of 5 average rating, 189 reviews

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.

Guest favorite

Guesthouse in Barnstable

4.94 out of 5 average rating, 17 reviews

Sweet Millie Guesthouse

Kick back and relax in this calm and stylish space where Barnstable, Mashpee, and Sandwich meet. This open concept bedroom/living area with queen sized bed is perfect for your Cape Cod getaway. Conservation and trails right in the neighborhood. Private entrance and private deck to enjoy the fall evenings, full kitchen, washer/dryer. Plenty of parking. Mashpee Commons, Mashpee beaches, Sandwich restaurants, Sandy Neck beach, Hyannis restaurants and beaches all within 10-15 minute drive.

Superhost

Guesthouse in Pocasset

4.78 out of 5 average rating, 153 reviews

Rustic Carriage House by the Sea

This is an authentic small old Cape Cod rustic carriage House. Which is charming, antique and unique. It is in a beautiful one-of-a-kind location. Loaded with cozy fun. A great getaway any time of the year! The Carriage house is walking distance away from beautiful Hens cove and is near many activities, Bike paths, the canal, the ferry, hiking, fishing, and many restaurants. Great for pet friendly Families, a couple of couples, friends that want to stay together, and bigger groups.

Guest favorite

Guesthouse in Yarmouth

4.96 out of 5 average rating, 211 reviews

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.

Guest favorite

Guesthouse in Sagamore Beach

4.99 out of 5 average rating, 321 reviews

The Guest House

The Guest House is free standing with a private entrance, loads of amenities and less than 300 yards from Cape Cod Bay. The two-story, farmhouse exterior has an open floor plan, modern cottage design, fully equipped kitchen, and private courtyard with Weber grill, wood fireplace and dedicated driveway. Guest privacy is a priority. Dogs under 75lbs welcome. There is a onetime fee of $150. This includes emotional support animals (ESA).

Guest favorite

Guesthouse in Barnstable

4.86 out of 5 average rating, 124 reviews

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 fire pit. Just a short walk to the ocean, beaches, the library and the general store.

Guest favorite

Guesthouse in Yarmouth

4.96 out of 5 average rating, 184 reviews

“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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Dennis guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guesthouse in Wellfleet

5 out of 5 average rating, 18 reviews

Peaceful, Family-Friendly Cottage, w/Private Beach

Guest favorite

Guesthouse in Dennis Port

4.85 out of 5 average rating, 261 reviews

Joe's Beach Hideaway

Guest favorite

Guesthouse in Barnstable

4.9 out of 5 average rating, 59 reviews

Osterville Guest House

Guesthouse in Eastham

4.82 out of 5 average rating, 11 reviews

Cozy 2 bedroom home near Rock Harbor/ bike trail

Guest favorite

Guesthouse in Falmouth

4.72 out of 5 average rating, 68 reviews

COZY GUESTHOUSE

Private room in North Eastham

4.86 out of 5 average rating, 73 reviews

Rugosa Guest House - Room 4

Private room in North Eastham

4.84 out of 5 average rating, 127 reviews

Rugosa Guest House - Room 5

Guesthouse in Yarmouth Port

4.97 out of 5 average rating, 59 reviews

Guest cabin in the woods

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Guest house rentals with a patio

Guest favorite

Guesthouse in Pocasset

5 out of 5 average rating, 65 reviews

Waterfront Cottage / Your Cape Escape

Guest favorite

Guesthouse in Chatham

4.96 out of 5 average rating, 23 reviews

Carriage House - Oyster Pond, Steps to Beach+Town

Guest favorite

Guesthouse in Brewster

5 out of 5 average rating, 10 reviews

Claw Foot Tub & King Bed at Club Tanuki Cottage

Guest favorite

Guesthouse in Forestdale

5 out of 5 average rating, 15 reviews

the Elevated Escape

Guesthouse in Barnstable

4.65 out of 5 average rating, 17 reviews

Beach glamping at the Zen Den

Guest favorite

Guesthouse in Yarmouth

5 out of 5 average rating, 24 reviews

Cozy Cottage

Guest favorite

Guesthouse in Orleans

5 out of 5 average rating, 19 reviews

Walk to Rock Harbor, The Loft at Rock Harbor Art

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Guest house rentals with a washer and dryer

Guest favorite

Guesthouse in Harwich Port

4.95 out of 5 average rating, 20 reviews

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

Guest favorite

Guesthouse in Sandwich

4.97 out of 5 average rating, 62 reviews

Private 1 king bedroom guest house-2021 built

Guest favorite

Guesthouse in West Yarmouth

5 out of 5 average rating, 36 reviews

Cozy, renovated home in a charming duplex cottage

Guest favorite

Guesthouse in Brewster

4.94 out of 5 average rating, 77 reviews

Cape Cod Cottage: Walk to the Beach in Brewster!

Guesthouse in Yarmouth

4.87 out of 5 average rating, 15 reviews

Carriage house in historic district,walk to beach!

Guesthouse in Centerville

4.86 out of 5 average rating, 86 reviews

Guest Cottage

Guest favorite

Guesthouse in Brewster

4.99 out of 5 average rating, 67 reviews

Brand new, on a swimmable pond

Guest favorite

Guesthouse in Brewster

4.89 out of 5 average rating, 45 reviews

Cape Cod beach inspired “Makondo” Suit Apartment!

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Quick stats about guesthouse rentals in Dennis

Total rentals
20 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
1.4K reviews
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
West Dennis Beach, Whydah Pirate Museum, and Sesuit Harbor Cafe

Guesthouse vacation rentals in Dennis

Top-rated guesthouse rentals in Dennis

Vacation rentals for every style

Apartments

Cottages

Houses

Popular amenities for Dennis guesthouse rentals

Family-friendly guest house rentals

Guesthouse in Wellfleet

Guesthouse in Dennis Port

Guesthouse in Barnstable

Guesthouse in Eastham

Guesthouse in Falmouth

Private room in North Eastham

Private room in North Eastham

Guesthouse in Yarmouth Port

Guest house rentals with a patio

Guesthouse in Pocasset

Guesthouse in Chatham

Guesthouse in Brewster

Guesthouse in Forestdale

Guesthouse in Barnstable

Guesthouse in Yarmouth

Guesthouse in Orleans

Guest house rentals with a washer and dryer

Guesthouse in Harwich Port

Guesthouse in Sandwich

Guesthouse in West Yarmouth

Guesthouse in Brewster

Guesthouse in Yarmouth

Guesthouse in Centerville

Guesthouse in Brewster

Guesthouse in Brewster

Quick stats about guesthouse rentals in Dennis

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore