
House holiday rentals in Middlesex County
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Top-rated house rentals in Middlesex County
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Luxe Bolton Lake
Stay at Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a beautiful waterfront, 3 bedrooms/3 full bathrooms and a year-round outdoor jacuzzi. Also included: gorgeous primary bedroom suite, artistic furnishings, cozy fireplace, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, kayaks, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

Entire House Magical Waterfront Getaway
4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this 3 bedrooms 2 baths well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Beautiful lakefront home, 4bed 2.5ba
Fully renovated, on 80ft of lake front. Perfect for summer water activities, stunning fall foliage and often ice skating in the winter! East-facing with stunning sunrises. Very well equipped kitchen, cosy sitting room with wood-burning stove, dining room for 8, and powder room. Large porch faces the lake, with a sitting area, and dining table for 8. Ground floor king-size master & bathroom, with stunning lake views. Upstairs, 3 queen bedrooms, all with lake views and ample closet space.

Beautiful Lake House on Lake Pocotopaug
Enjoy a relaxing vacation in a beautiful, updated lakefront home on Lake Pocotopaug. Summer =grilling out, kayaking & paddle boarding with family & friends. A lakeside marina offers party boat rides & kayak rentals. Winter=relaxation by the cozy fireplace, games and ice skating when the lake freezes over. Projector Screen, Games, Books, AC, Heat, Outdoor Grill and a working fireplace. All year round, we'd love to have you at our home. which we love and use as a getaway from the city.

Stunning Artisan Waterfall Escape, Walk Downtown
Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

The Farmhouse
Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Amazing 2BR Riverfront Gem
Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more.

Casino Stay & Play House w/Hot Tub, Game Room
Come have an unforgettable vacation at our fun-packed home! The house is loaded with of games and conveniently located close to Mohegan Sun, Foxwoods, Mystic, Vineyards, Navel Submarine Base, Ct College and several beaches. Enjoy our game room where you can sing karaoke, play over 3,000 classic games and draw on our giant chalk board wall. Outside enjoy swimming in your own private pool, take dip in the hot tub, play a game of corn hole and watch tv by the fire pit on the deck

Cozy Comforts!
Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Best of both worlds!
Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!
Popular amenities for house rentals in Middlesex County
House rentals with a pool

Private Oasis W/Stunning Vinyard and Pool Views

3 BR/Pool. Walk to Beach & Town!

Breathtaking home with unforgettable views & pool!

Serenity + privacy; 1 block to waterfront dining

East Hampton Oasis - Pool and Hot Tub

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Explore the Water & Woods at a Relaxing Retreat

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Weekly house rentals

Adorable Beach House on LI Sound

Scenic Mulberry Point Connecticut Beach House

Cozy beach cottage close to everthing

Soundscape Beachfront House!

Stylish Modern Home, 4-Bedroom, Madison CT

Ideal Historic Home in Essex Village

“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach

Historic House by the River
Private house rentals

The Gait House at High Gait Farm

Fortune Retreat

Coast and Country Private Estate

Backyard Tiny House in the Woods

The Dollhouse Mystic, Casinos, Beaches, Parks

Remodeled cozy home near beach

Large private estate

Cozy Cape on the Cove
Destinations to explore
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- Beachfront rentals Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with breakfast Middlesex County
- Flat rentals Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Rentals with an EV charger Middlesex County
- Rentals with lake access Middlesex County
- Bed and breakfasts Middlesex County
- Rentals with a kayak Middlesex County
- Guest house rentals Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a firepit Middlesex County
- Rentals with a hot tub Middlesex County
- Private suite rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with a patio Middlesex County
- Rentals with pools Middlesex County
- Rentals with beach access Middlesex County
- House rentals Connecticut
- House rentals United States
- Beach
- Yale University
- Six Flags New England
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- East Matunuck State Beach
- Mohegan Sun
- Southampton Beach
- Ocean Beach Park
- Foxwoods Resort Casino
- Mystic Seaport Museum
- Hammonasset Beach State Park
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Blue Shutters Beach
- Ski Sundown
- Wölffer Estate Vineyard
- University of Connecticut
- Mount Southington Ski Area
- Orient Beach State Park
- Ocean Beach





