House holiday rentals in Middletown

WeHa Penthouse w/ Private Deck

Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

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.

Luxe Bolton Lake

Lakefront jacuzzi for fall! Relax and enjoy the stylish comfort of our 3 bedroom/3 bathroom architecturally-designed lake home. The Luxe lake house features an expansive waterfront, outdoor jacuzzi, gorgeous primary bedroom suite w/ private shower and tub, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, fast WiFi, large deck, fire pit, kayaks, vintage aluminum canoe, board games, and much more. Come stay at the Luxe lake house and make memories that will last a lifetime!

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom newly updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (month of July). Wi-Fi/cable, central AC/hot air, washer/dryer, and grill are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey table) are provided. This house is truly relaxing and will feel like home.

Connecticut Chalet: Experience Fall in New England

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

Cozy Mid Century home in prime location!

Enjoy an updated, mid century modern inspired, home minutes away from Wesleyan University & TPC River highlands! This eclectic space offers you a cozy retreat that is centrally located. The bedrooms have 1 King, 1 Queen, & 1 Full with luxury mattresses! High speed Wi-Fi, chefs kitchen, dedicated work desk, and garage space! A few mins from RT 9 & 91! Easy to get everywhere in CT!!! Only 5 mins to TPC, 10 mins to Wesleyan, 20 mins to Hartford! Scald protector on shower upstairs!

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!

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This beautiful home includes an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large bathroom with spa like jets. His and hers closets. Beautiful kitchenette. 50 inch T.V., Free WiFi. , comfortable dining and more, all for the comfort and convenience of our guests.