House vacation 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.

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Guest favorite

Home in Old Lyme

4.9 out of 5 average rating, 115 reviews

The Beach House

Our Beach House is close to the mouth of the Connecticut River surrounded by the salt marsh and at the end of our street you can see Old Saybrook lighthouses. Quaint local towns, two major shopping outlets and award winning casinos. Close to Gillette Castle, Mystic Seaport and the Coast Guard Academy. Lots of restaurants serving up local fare. Beautiful beaches, theater, music, and a variety of activities (kayaking, hiking, bird watching). Many museums in both directions on I-95 and I-91.

Nov 25 – Dec 2

ﺩ.ﺇ861 per night

Guest favorite

Home in Old Saybrook

4.96 out of 5 average rating, 104 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Aug 28 – Sep 4

ﺩ.ﺇ1,431 per night

Superhost

Home in East Hampton

4.87 out of 5 average rating, 114 reviews

Lakehouse, 4 bedrms, winter discounts available

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.

Oct 6 – 13

ﺩ.ﺇ1,544 per night

Guest favorite

Home in Chester

4.98 out of 5 average rating, 197 reviews

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.

Nov 16 – 23

ﺩ.ﺇ1,217 per night

Guest favorite

Home in Guilford

4.89 out of 5 average rating, 38 reviews

Guilford cozy in-law apt with private entrance

Our apt is close to I95, 2 hrs from NYC, 25 mins. from New Haven, 2 1/2 hrs from Newport, RI, 3 hrs from Boston, MA, 45 mins from Hartford, CT. Guilford is a shoreline town and a convenient location from which to take many day trips. You’ll love our place because it sits in a wooded setting on an interior lot. We have an outdoor seating area with a replace, under roof. And, yet we are 5 mins. to the highway access. Our apartment is good for couples, solo adventurers, and business travelers.

Oct 15 – 22

ﺩ.ﺇ585 per night

Guest favorite

Home in Clinton

4.97 out of 5 average rating, 173 reviews

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.

Sep 18 – 25

ﺩ.ﺇ1,008 per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 9 reviews

The Farmhouse Stay

Designed to be your very own home away from home. At The Farmhouse Stay, we’ve honored its history and all that makes it special, while thoughtfully tucking in modern additions to create a cozy, contemporary environment for today’s houseguest. The Farmhouse Stay is a 1780 cape situated on 15 quiet acres. The 2,000 square ft home features 2 bedrooms, 2 bathrooms, an eat-in kitchen, butler’s pantry, living room, formal dining room, dedicated laundry room, and an upper level landing.

Jun 9 – 16

ﺩ.ﺇ2,146 per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 78 reviews

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!

Dec 22 – 29

ﺩ.ﺇ411 per night

Guest favorite

Home in Lyme

4.91 out of 5 average rating, 292 reviews

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

Dec 28 – Jan 4

ﺩ.ﺇ1,305 per night

Guest favorite

Home in Lyme

4.97 out of 5 average rating, 190 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature

May 19 – 24

ﺩ.ﺇ980 per night

Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 257 reviews

Modern Luxurious CT Country Home

Beautiful mid-century modern glass and wood house in the forest, featuring tranquil designer spaces and continuously updated amenities. With only 2 hours from New York City and Boston, by train or by car, this is the ideal sanctuary for a perfect getaway. Minimum 2 nights during fall through spring months, 3 to 5-nights minimum in the summer months.

Jan 23 – 30

ﺩ.ﺇ1,536 per night

Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 128 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Feb 8 – 15

ﺩ.ﺇ1,491 per night