House holiday 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Old Lyme

4.9 out of 5 average rating, 125 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.

Guest favourite

Home in East Haddam

5 out of 5 average rating, 23 reviews

Pine Pond at Devils Hopyard State Park

New renovated post and beam farm style private home. Located 1/2 mile off a rural town road. 15 wooded acres abutting Devils Hopyard State Park. Includes a private 5 acre pond for fishing, kayaking, rowboat, peddle boat. Located about 8 minutes drive from Fox Hopyard Golf Course. Interior newly renovated kitchen with new appliances, spacious island with eating area. Dining area has a huge custom made live edge pine slab table and matching benches. This table can easily accommodate 14 people.

Guest favourite

Home in Old Saybrook

4.97 out of 5 average rating, 120 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

Guest favourite

Home in East Haddam

4.98 out of 5 average rating, 45 reviews

Spacious 5 bdrm, 6 bth, pool-hot tub, game room

Spacious 5 bedroom 6 bath sleeps 14 -WHAT YOU’LL LOVE- • Private resort style patio, including STUNNING POOL, HOT TUB, fireplace and firepit, bar and grill, 65" TV, outdoor bathroom and shower. • Open concept floor plan that is great for groups and families. • Authentic New England experience. • Fun game room for adults and kids with wet bar and mini fridge • Quiet street and neighborhood. NY times listed East Haddam in their “52 places to love” in 2021 1 mile to East Haddam Center

Guest favourite

Home in Clinton

4.94 out of 5 average rating, 131 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views. Come experience the charm of New England this winter. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, and warm charming décor. Only minutes to groceries, coffee shops, beaches and amazing CT scenery at almost every turn. Other favorites include Chamard Vineyard, Shopping Outlets, Essex Steam Train, fantastic Restaurants with music, and lots more!

Guest favourite

Home in East Haddam

4.94 out of 5 average rating, 182 reviews

Romantic Getaway at The Lake!

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 Hartford, 30 minutes from the Mohegan Casino.

Superhost

Home in Clinton

4.69 out of 5 average rating, 83 reviews

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens

Welcome to your dream waterview getaway! Our property offers the perfect blend of two private beaches 4 houses away. An 8-minute walk will take you to a public beach with a playground area, basketball court, grill, and pavilion. It's the ideal spot for a fantastic day by the water. Your beds will be made up with fresh linens, and towels ready for your comfort. We've even offer beach towels and provide chairs, making it easy for you to relax and soak up the sun without the hassle of packing.

Guest favourite

Home in Clinton

4.97 out of 5 average rating, 191 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.

Guest favourite

Home in Lyme

4.92 out of 5 average rating, 325 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.

Superhost

Home in Lebanon

4.84 out of 5 average rating, 25 reviews

Breathtaking Lake Williams Lakefront

Relax lakefront with the whole family at this peaceful, private seasonal retreat. Expansive double lot lakefront with 125’ of direct waterfront and steps into lake. Fishing, kayaking and paddle boarding. Daydream in the large custom outdoor shower overlooking the lake with private changing area. Then, barbecue and have a wiffle ball game while overlooking the lakefront at sunset. There's even a boat house with couch and TV looking out to the water!

Superhost

Home in Clinton

4.91 out of 5 average rating, 11 reviews

Clinton Beach House & Cottage w/ Pool, Near Shore

A block and a half from the water and marinas! Beautiful 4BR/2.5 BA beach area home (sleeps 10), close to marina/town beach. Property includes in-ground pool and 1BR/1BA guest house (sleeps 4). A spacious colonial-style main house and carriage house share a bright sunny half-acre. Fully fenced in backyard makes it idea for families. Backyard fire-pit, new plantings, beach stone, window boxes, and an outdoor shower add to the property's appeal.

Guest favourite

Home in Clinton

4.97 out of 5 average rating, 119 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

REDUCED RATES: Feb '25 - Mar '25 INSTANT BOOK NOW = WINTER 2 & 3 DAY MIN Feb '25 - Sept '25 All Open Availability + SUMMER '25 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