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
Sep 24 – Oct 1
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Sep 11 – 18
Guesthouse in Southampton
4.95 out of 5 average rating, 412 reviewsTiny Home in Prime Spot in Southampton Village
Oct 7 – 14
Guesthouse in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Jan 17 – 24
Guesthouse in Mystic
4.78 out of 5 average rating, 90 reviewsMaxson House - a serene and stylish getaway
Oct 24 – 31
Guesthouse in New London
4.98 out of 5 average rating, 97 reviewsFully Renovated, Ocean Views, Fireplace & Beach
Dec 24 – 31
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
Apr 23 – 30
Guesthouse in Sprague
4.97 out of 5 average rating, 189 reviewsHouse on Little River / Writer Retreat
Aug 29 – Sep 5
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
Jan 9 – 16
Guesthouse in Madison
4.95 out of 5 average rating, 56 reviewsThe Rising Tide Cottage
Aug 30 – Sep 4
Guesthouse in Norwich
5.0 out of 5 average rating, 25 reviewsHistoric Guest Suite
Sep 28 – Oct 5
Guesthouse in Pomfret
5.0 out of 5 average rating, 20 reviewsCottage in Quiet Corner. Four miles from town.
Nov 14 – 21
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Aug 3 – 10
Guesthouse in Hampton Bays
4.91 out of 5 average rating, 43 reviewsQuaint One Bedroom Cottage with Private Entrance
Jan 25 – Feb 1
Guesthouse in Bridgehampton
4.83 out of 5 average rating, 63 reviewsCentral Hamptons Guesthouse
Dec 12 – 19
Guesthouse in Calverton
4.96 out of 5 average rating, 28 reviewsPrivate Luxe Cottage at Gates of Wine Country
Apr 20 – 27
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
Jul 23 – 30
Guesthouse in New Haven
4.94 out of 5 average rating, 241 reviewsSquare 6ix
Oct 16 – 23
Guesthouse in Southold
4.95 out of 5 average rating, 41 reviewsSouthold- Adorable 1 Bedroom Cottage
Jun 10 – 17
Guesthouse in Mystic
5.0 out of 5 average rating, 93 reviewsHERON HOUSE MYSTIC, CT.
Feb 14 – 21
Guesthouse in Southampton
4.88 out of 5 average rating, 43 reviewsModern Guesthouse
Jun 9 – 16
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
Jul 30 – Aug 6
Guesthouse in Branford
Sunset Studio
Jul 23 – 30
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
May 15 – 22
Destinations to explore
- Guesthouse rentals New York
- House rentals New York
- House rentals United States
- Guesthouse rentals United States
- House rentals Manhattan
- Guesthouse rentals Manhattan
- Guesthouse rentals Boston
- House rentals Boston
- House rentals Connecticut
- Guesthouse rentals Connecticut
- Kid-friendly rentals Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with lake access Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with breakfast Middlesex County
- Rentals with a fire pit Middlesex County
- Monthly Rentals Middlesex County
- Pet-friendly rentals Middlesex County
- House rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Beachfront rentals Middlesex County
- Rentals with pools Middlesex County
- Rentals with a washer and dryer Middlesex County
- Private suite rentals Middlesex County
- Family-friendly rentals Middlesex County
- Bed and breakfasts Middlesex County
- Apartment rentals Middlesex County
- Rentals with a hot tub Middlesex County
- Rentals with an EV charger Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Rentals with a patio Middlesex County
- Rentals with beach access Middlesex County
- 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