Guesthouse vacation rentals in Middlesex County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Middlesex County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Groton
4.94 out of 5 average rating, 386 reviewsQuiet studio with sleeping loft and deck
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Guesthouse in Southampton
4.95 out of 5 average rating, 412 reviewsTiny Home in Prime Spot in Southampton Village
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Guesthouse in Mystic
4.78 out of 5 average rating, 90 reviewsMaxson House - a serene and stylish getaway
Guesthouse in New London
4.98 out of 5 average rating, 97 reviewsFully Renovated, Ocean Views, Fireplace & Beach
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
Guesthouse in Sprague
4.97 out of 5 average rating, 189 reviewsHouse on Little River / Writer Retreat
Guest house rentals with a patio
Guesthouse in Norwich
5.0 out of 5 average rating, 4 reviewsBrand new & close to casinos with HOT TUB
Guesthouse in Madison
4.95 out of 5 average rating, 56 reviewsThe Rising Tide Cottage
Guesthouse in Norwich
5.0 out of 5 average rating, 25 reviewsHistoric Guest Suite
Guesthouse in Pomfret
5.0 out of 5 average rating, 20 reviewsCottage in Quiet Corner. Four miles from town.
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Guesthouse in Hampton Bays
4.91 out of 5 average rating, 43 reviewsQuaint One Bedroom Cottage with Private Entrance
Guesthouse in Bridgehampton
4.83 out of 5 average rating, 63 reviewsCentral Hamptons Guesthouse
Guesthouse in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Guest house rentals with a washer and dryer
Guesthouse in Glastonbury
4.96 out of 5 average rating, 133 reviewsUnique luxurious private building in historic area
Guesthouse in New Haven
4.94 out of 5 average rating, 241 reviewsSquare 6ix
Guesthouse in Southold
4.95 out of 5 average rating, 41 reviewsSouthold- Adorable 1 Bedroom Cottage
Guesthouse in Mystic
5.0 out of 5 average rating, 93 reviewsHERON HOUSE MYSTIC, CT.
Guesthouse in Southampton
4.88 out of 5 average rating, 43 reviewsModern Guesthouse
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
Guesthouse in Branford
Sunset Studio
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
Destinations to explore
- House rentals New York
- Guesthouse rentals New York
- House rentals United States
- Guesthouse rentals United States
- Guesthouse rentals Manhattan
- House rentals Manhattan
- House rentals Boston
- Guesthouse rentals Boston
- House rentals Connecticut
- Guesthouse rentals Connecticut
- Rentals with lake access Middlesex County
- Rentals with a patio Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Rentals with pools Middlesex County
- Bed and breakfasts Middlesex County
- Rentals with breakfast Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with a fire pit Middlesex County
- Rentals with a hot tub Middlesex County
- Apartment rentals Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with an EV charger Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with a washer and dryer Middlesex County
- Monthly Rentals Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Beachfront rentals Middlesex County
- Rentals with beach access Middlesex County
- Kid-friendly rentals Middlesex County
- House rentals Middlesex County
- Private suite rentals Middlesex County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes