Cottage vacation rentals in Middlesex County

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Middlesex County

Guests agree: these cottages are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Lebanon

4.86 out of 5 average rating, 136 reviews

Go Jump in the Lake!

NEWLY RENOVATED FOR THE 2023 SEASON! Our lake house is situated on 1.5 acres just 250 steps to the Cove Road boat launch on beautiful Amston Lake. The lake is a pristine 188-acre retreat located in Lebanon and Hebron, CT. Swimming, kayaking, canoeing, paddle boarding, fishing, and sunbathing are all activities you can enjoy. There are no motor boats allowed so you can enjoy all of those activities in a peaceful environment. Two beaches are located 1/2 or 1 mile away with ample parking at both

Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 159 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 245 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Guest favorite

Cottage in Deep River

5.0 out of 5 average rating, 9 reviews

Serene Waterfront Cottage

Welcome to Smuggler’s Cove Cottage. Rumor has it that this quaint cottage was once the scene of infamous rum running. Today, it’s our little slice of heaven away from the chaotic city life. It’s the perfect place to curl up and read a book by the fire when it’s chilly out. During the warmer months, take full advantage of the spacious waterfront patio & docks. Whether you’re sunbathing or having a drink watching the local geese and ducks float by, this tranquil cottage has everything you need.

Guest favorite

Cottage in Hebron

4.9 out of 5 average rating, 88 reviews

Welcome to The Holly at Amston Lake

Welcome to The Holly at Amston Lake! Great two-bedroom cottage situated in a peaceful lake community. Great place to enjoy time with family and friends. Take a stroll down to the main beach or enjoy the great views of the lake from the deck! Don't forget about the gas fire pit for those chilly evenings. We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit, kayaks, and two main beaches.

Guest favorite

Cottage in Chester

4.98 out of 5 average rating, 229 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Guest favorite

Cottage in Guilford

5.0 out of 5 average rating, 82 reviews

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Guest favorite

Cottage in Old Saybrook

4.97 out of 5 average rating, 75 reviews

Belle Vue Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Guest favorite

Cottage in Middlefield

4.93 out of 5 average rating, 230 reviews

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

Guest favorite

Cottage in Deep River

4.87 out of 5 average rating, 23 reviews

Country Cottage in Private Garden Setting

We are located in a small country town in Connecticut, in a private garden setting tucked away in a forested area of Deep River. Woodfun Gardens is a garlic growing farm, I plant and harvest garlic for garlic salt which we sell online. We will leave you a jar, you can take home and enjoy. If you like it you can purchase more on our website. The property is surrounded by many marked trails for hiking or walking your dog, or just peace and quiet.

Guest favorite

Cottage in Madison

5.0 out of 5 average rating, 102 reviews

Shabby Chic Retreat

Welcome to Greenfield Cottage! We are located in a quiet neighborhood close to the town village and beaches. Hammonasset State Park & Beach is about 4 miles from us. Chatfield Hollow is also nearby. When in CT we stay in the studio apt on the lower level of the cottage. It has a separate entrance & garden space and is soundproof. PLEASE NOTE: The pet fee is $25/night, per pet (not per stay). Laundry Rm is accessible to guests and hosts.

Superhost

Cottage in Deep River

4.73 out of 5 average rating, 222 reviews

Cottage overlooking the CT river

Adorable 1800 cottage with views of the CT River. Upstairs bedroom with a king. Bathroom with a tub and a tiny kitchen. Other room is used as an office but has a queen pull out bed. Watch the Essex steam train, Becky Thatcher riverboat, or hang out at the river, bring your kayaks or paddleboards as there is a boat ramp right across the street.