
House vacation 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.

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.

Amazing 2BR Riverfront Gem
Unwind at this happy getaway with an amazing river view, peaceful neighborhood, and in the heart of fall foliage and holiday scenes. 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, and lots more.

“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!

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 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).

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON
INSTANT BOOK: Apr 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Family Stays, CT
Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our welcoming home is an ideal choice for families, solo travelers, couples, professionals, business travelers, and almost anyone. Whether you're here to explore Middletown or the surrounding Connecticut towns, you'll have the entire property to yourself for a comfortable and enjoyable stay.
Popular amenities for Middlesex County house rentals
House rentals with a pool

Breathtaking home with unforgettable views & pool!

Killingworth Estate - Elite Amenities & Finishings

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

Waterfront Beach House with pool

Stunning Views, Bucolic Bliss in 1790s Farmhouse

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

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

mid century ranch style house on farmland
Weekly house rentals

Tinker Gardens

Pet Friendly Cozy Home for Work/Leisure

Boulder Lake House Retreat

Waterfront Lake House on Pickerel Lake

Private 1-Bdrm Apt in West Haven

Winter at the Haddam House

Essex village carriage house

Coastal Getaway - walk to town and waterfront
Private house rentals

Zion's Light Beach Cottage

Private Entire Home • Close to New Haven & Shore

New England shoreline charm, private beach access

5 Star Branford Cozy Cottage

Mulberry Seaside Cottage

Elegant Countryside Estate

Quiet CT Country Escape | Cozy & Historic

Old Lyme Farmhouse
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Cottage rentals Middlesex County
- Waterfront rentals Middlesex County
- Bed and breakfasts Middlesex County
- Guesthouse rentals Middlesex County
- Rentals with lake access Middlesex County
- Rentals with breakfast Middlesex County
- Rentals with an EV charger Middlesex County
- Apartment rentals Middlesex County
- Rentals with a fire pit Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Family-friendly rentals Middlesex County
- Private suite rentals Middlesex County
- Rentals with a kayak Middlesex County
- Beachfront rentals Middlesex County
- Rentals with beach access Middlesex County
- Rentals with pools Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with a washer and dryer Middlesex County
- Rentals with a hot tub Middlesex County
- Rentals with a patio Middlesex County
- Fitness-friendly rentals Middlesex County
- House rentals Connecticut
- House rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- East Matunuck State Beach
- Long Island Aquarium
- Hammonasset Beach State Park
- Mystic Seaport Museum
- Mount Southington Ski Area
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Burlingame State Park
- Yale University Art Gallery
- Ski Sundown
- Orient Beach State Park
- East Hampton Main Beach
- Meschutt Beach
- Wölffer Estate Vineyard
- Bluff Point State Park




