
House holiday rentals in Middlesex County
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Top-rated house rentals in Middlesex County
Guests agree: these houses are highly rated for location, cleanliness and more.

Niantic River Beach Cottage | Waterviews
Kick back and relax in this quiet, stylish New England beach cottage with water views, a private neighborhood beach, an outdoor shower, and a sunny patio for coffee or evening wine. Just minutes from downtown Niantic, you’ll find beaches, cafés, bakeries, ice-cream stands, seafood, boutiques, boat launches, trails, outdoor concerts, and more—all within a short drive or bike ride. Perfect for a romantic getaway, a family weekend, or some quiet coastal downtime. See why guests love staying here!

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.

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.

Connecticut Chalet: Winter Nights by the Fire
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.

Lake Home w/Game Room 5 Min To Foxwoods & Mohegan
Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 5 min. from Foxwoods, 10 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

“The Lighthouse” A Beach Cottage by the Sea!
Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Welcome to The Avery!
Welcome to The Avery at Amston Lake! Great three-bedroom lake cottage situated in a peaceful lake community. Great place to slow down and relax. Lay out in the sun on the beach, enjoy a fire in the backyard, and even spend some time playing games in the cozy sun room! We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit area, two kayaks located at the kayak launch, and two main beaches.

Waterside Beach Retreat
Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

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 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!

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).
Popular amenities for house rentals in Middlesex County
House rentals with a pool

FREE Private Indoor Heated Pool - Mystic Home

Spacious 4 bedroom, oasis with ocean views galore

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

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Casino Stay & Play House w/Hot Tub, Game Room

mid century ranch style house on farmland

Beauty and the Beach!
Weekly house rentals

Adorable Beach House on LI Sound

Boulder Lake House Retreat

Killingworth Estate - Elite Amenities & Finishings

Stylish Modern Home, 4-Bedroom, Madison CT

Coastal Getaway - walk to town and waterfront

Mulberry Seaside Cottage

4 Bedrooms Modern Home with Water View & Access

The Farmhouse Stay
Private house rentals

"Sunset Shores" Lakeside Oasis

Waterfront Lake House on Pickerel Lake

Private Entire Home • Close to New Haven & Shore

Historic Haskell House 1700s Get Away!

Winter at the Haddam House

Guilford cozy in-law apt with private entrance

Elegant Countryside Estate

Great Hammock Getaway | Beaches, Views & Hot Tub
Destinations to explore
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- Rentals with breakfast Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Rentals with a fireplace Middlesex County
- Beachfront rentals Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with lake access Middlesex County
- Private suite rentals Middlesex County
- Rentals with pools Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with outdoor seating Middlesex County
- Flat rentals Middlesex County
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Bed and breakfasts Middlesex County
- Guest house rentals Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with a firepit Middlesex County
- Rentals with a hot tub Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with a patio Middlesex County
- Rentals with an EV charger Middlesex County
- Rentals with beach access Middlesex County
- House rentals Connecticut
- House rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- Groton Long Point Main Beach
- Cedar Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Napeague Beach
- Amagansett Beach
- Jennings Beach
- Wildemere Beach
- Sandy Beach
- Seaside Beach
- Ninigret Beach




