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 Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
Mar 27 – Apr 3
Guesthouse in Groton
4.94 out of 5 average rating, 385 reviewsQuiet studio with sleeping loft and deck
Sep 8 – 15
Guesthouse in Southampton
4.95 out of 5 average rating, 411 reviewsTiny Home in Prime Spot in Southampton Village
Oct 18 – 25
Guesthouse in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
Oct 13 – 20
Guesthouse in Mystic
4.78 out of 5 average rating, 90 reviewsMaxson House - a serene and stylish getaway
Oct 19 – 26
Guesthouse in New London
4.98 out of 5 average rating, 97 reviewsFully Renovated, Ocean Views, Fireplace & Beach
Oct 27 – Nov 3
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
Mar 19 – 26
Guesthouse in Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
Mar 2 – 9
Guest house rentals with a patio
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, 23 reviewsHistoric Guest Suite
Aug 9 – 16
Guesthouse in Pomfret
5.0 out of 5 average rating, 20 reviewsCottage in Quiet Corner. Four miles from town.
Jan 19 – 26
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
Aug 18 – 25
Guesthouse in Bridgehampton
4.82 out of 5 average rating, 61 reviewsCentral Hamptons Guesthouse
Jul 2 – 9
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
Sep 10 – 17
Guesthouse in Norwich
New place to stayBrand new & close to casinos with HOT TUB
Aug 7 – 14
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
Oct 19 – 26
Guesthouse in New Haven
4.94 out of 5 average rating, 241 reviewsSquare 6ix
Oct 10 – 17
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
May 9 – 16
Guesthouse in Mystic
5.0 out of 5 average rating, 93 reviewsHERON HOUSE MYSTIC, CT.
Dec 5 – 12
Guesthouse in Southampton
4.88 out of 5 average rating, 42 reviewsModern Guesthouse
Jun 7 – 14
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
May 27 – Jun 3
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
May 9 – 16
Guesthouse in Clinton
4.94 out of 5 average rating, 192 reviewsThe Gardener's Cottage Dog friendly/ weekly/montly
Sep 26 – Oct 3
Destinations to explore
- Guesthouse rentals New York
- House rentals New York
- Guesthouse rentals United States
- House rentals United States
- Guesthouse rentals Manhattan
- House rentals Manhattan
- House rentals Boston
- Guesthouse rentals Boston
- Guesthouse rentals Connecticut
- House rentals Connecticut
- House rentals Middlesex County
- Beachfront rentals Middlesex County
- Rentals with pools Middlesex County
- Kid-friendly rentals Middlesex County
- Rentals with lake access Middlesex County
- Bed and breakfasts Middlesex County
- Family-friendly rentals Middlesex County
- Monthly Rentals Middlesex County
- Rentals with breakfast Middlesex County
- Rentals with an EV charger Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with a patio Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a kayak Middlesex County
- Private suite rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Apartment rentals Middlesex County
- Waterfront rentals Middlesex County
- Cottage rentals Middlesex County
- Rentals with beach access Middlesex County
- Rentals with a washer and dryer Middlesex County
- Rentals with a fire pit Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with a hot tub 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