House holiday rentals in Middlesex County
Find and book unique houses on Airbnb
Top-rated house rentals in Middlesex County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Middlesex County
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 119 reviewsPool House
Home in Montville
4.91 out of 5 average rating, 236 reviewsCasino Wine Down House***
Home in Manorville
4.99 out of 5 average rating, 205 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Sag Harbor
4.89 out of 5 average rating, 167 reviewsKiddo Approved! Heated Pool/Hotub Renovated Home
Home in Hampton Bays
4.98 out of 5 average rating, 113 reviewsBeach House Feel - newly renovated backyard Oasis
Home in East Hampton
4.93 out of 5 average rating, 142 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in East Hampton
4.92 out of 5 average rating, 130 reviewsHeated pool, games room, near beach, kid-friendly
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Weekly house rentals
Home in Haddam
5.0 out of 5 average rating, 10 reviewsThe Farmhouse Stay
Home in East Hampton
4.98 out of 5 average rating, 54 reviewsLake Fun: PingPong, Pool Table, Slide, EV Charger
Home in Essex
5.0 out of 5 average rating, 54 reviews4-Bedroom Farmhouse *Comfort and Privacy*
Home in Essex
4.97 out of 5 average rating, 36 reviewsIdeal Historic Home in Essex Village
Home in Old Saybrook
5.0 out of 5 average rating, 4 reviewsRomantic Couples Retreat with Private Sandy Beach
Home in Westbrook
5.0 out of 5 average rating, 40 reviewsHome Away From Home
Home in Clinton
5.0 out of 5 average rating, 18 reviewsSoundscape Beachfront House!
Home in East Hampton
4.88 out of 5 average rating, 24 reviewsWaterfront Lake House
Private house rentals
Home in Middletown
4.95 out of 5 average rating, 20 reviewsHot Tub and pool Home away from home
Home in Madison
5.0 out of 5 average rating, 17 reviewsNewly Renovated Beach Cottage!
Home in Westbrook
4.78 out of 5 average rating, 32 reviewsDuckling Crossing | Beach House on the Sand
Home in East Hampton
4.99 out of 5 average rating, 93 reviewsClassic Lake House~4 Steps to water_FirePit_kayaks
Home in East Hampton
4.92 out of 5 average rating, 25 reviewsA Relaxing Getaway Lake House
Home in East Haddam
4.94 out of 5 average rating, 16 reviewsHistoric Charm Meets Modern Comfort
Home in Old Lyme
5.0 out of 5 average rating, 17 reviews5* 5 bed Luxury CT beach for large groups/families
Home in Clinton
4.97 out of 5 average rating, 99 reviewsAmazing 2BR Riverfront Gem
Destinations to explore
- Tiny house rentals New York
- Townhouse rentals New York
- Guest house rentals New York
- Lakehouse rentals New York
- House rentals New York
- Beach house rentals New York
- Earth house rentals United States
- House rentals United States
- Guest house rentals United States
- Lighthouse rentals United States
- Townhouse rentals United States
- House rentals Manhattan
- Townhouse rentals Manhattan
- Guest house rentals Manhattan
- House rentals Boston
- Guest house rentals Boston
- Townhouse rentals Boston
- Beach house rentals Boston
- Tiny house rentals Connecticut
- Beach house rentals Connecticut
- House rentals Connecticut
- Guest house rentals Connecticut
- Lakehouse rentals Connecticut
- Townhouse rentals Connecticut
- Rentals with breakfast Middlesex County
- Rentals with a patio Middlesex County
- Fitness-friendly rentals Middlesex County
- Family-friendly rentals Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Bed and breakfasts Middlesex County
- Flat rentals Middlesex County
- Rentals with a firepit Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with a kayak Middlesex County
- Monthly Rentals Middlesex County
- Pet-friendly rentals Middlesex County
- Beachfront rentals Middlesex County
- Rentals with lake access Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with pools Middlesex County
- Rentals with a hot tub Middlesex County
- Rentals with beach access Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Rentals with an EV charger Middlesex County
- Private suite rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Guest house rentals 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