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Vacation rentals in Middlesex County

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Top-rated vacation rentals in Middlesex County

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

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Guesthouse in Essex

4.82 out of 5 average rating, 28 reviews

Privateers Boathouse (Village Waterfront)

Right in the middle of everything Essex Village has to offer. Very special little waterfront cottage with unrivaled views & access to town is hosting guests. Park your car off-street and enjoy all the wonders of Essex Village by foot during your visit. Secluded, yet utterly central Village location. Short drive to beaches, golf, hikes & more. 🌟 Request a WEEKLY rate 🌟 🛶 Access to swimming pool ONLY WITH ADVANCE ARRANGEMENT 🚣‍♀️ (No onsite kayaks/launch)

Home in Clinton

4.94 out of 5 average rating, 129 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway, with an amazing river view, in a 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.

Cottage in Guilford

4.93 out of 5 average rating, 264 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”.

Home in Old Saybrook

5 out of 5 average rating, 38 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.

Guesthouse in East Hampton

4.93 out of 5 average rating, 41 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull-out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and 2 paddle boards are available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways, family vacations, or visiting family locally.

Apartment in Madison

4.9 out of 5 average rating, 10 reviews

One Bedroom Apt-Cristys Madison

1 bedroom apt with king bed, 2 full bathrooms (1 w bathtub), full kitchen with keurig, living room and workspace. All couches pull out to beds (4 beds total). Free cable/Roku, WiFi and beach access. 1 minute walk from 2 beaches, and minutes from center of town, shopping and various weekly town events. Main building has a full restaurant with breakfast, lunch and dinner. Maid service not provided. Dog friendly - dog must be well behaved.

Cottage in Guilford

4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

A quintessential New England cottage with views of the water from all rooms. Spectacular sunrises and sunsets, enchanting panorama views. A stone's throw from the beautiful Grass Island state park and boat launch, a waterfront natural preserve, perfect for hiking or communing with nature. The interior underwent a full renovation in 2020 with new appliances and bath fixtures. Original structure preserved. A tranquil, quiet place.

Home in Westbrook

4.93 out of 5 average rating, 42 reviews

Private vacation home, close to beach

Welcome the our new Airbnb where serenity & style come together. Enjoy this charming, cozy home. Upon entering, you'll feel immediately relaxed & on vacation. This home is filled with natural sunlight light, large kitchen, stocked with with gourmet cookware & utensils. Outside you'll hear the babbling brook river, private large yard that offers outside patio deck for dining, entertaining or cuddling up by the fire pit.

Cottage in Old Saybrook

5 out of 5 average rating, 93 reviews

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.

Cottage in Hebron

4.92 out of 5 average rating, 100 reviews

The Blue Heron at Amston Lake

3 BEDROOM, quiet cottage near Amston Lake. 3 minute walk to private main beach. 1.5 bath with oversized shower stall. Sliding door leads to large, covered patio. Full, semi private large backyard. Hammock, bicycles, canoe, kayak, fire pit and grill provided. Ping pong table/dart board in basement. Close to Airline Trails, vineyards, breweries, casinos., state parks.

Home in East Hampton

4.89 out of 5 average rating, 38 reviews

A Relaxing Getaway Lake House

Welcome to our stunning and updated lakefront home on the picturesque Lake Pocotopaug! Nestled in a tranquil setting, this is the ultimate destination for a relaxing and unforgettable vacation. Whether you're seeking a summer getaway filled with water activities or a cozy winter retreat by the fireplace, our home offers it all.

Home in Madison

5 out of 5 average rating, 14 reviews

Beach Home & Garden Paradise

Beautiful Beach Home and Garden Paradise. Beautifully designed and Remodeled Beach home and 1/2 acre native garden paradise with incredible views of Long Island Sound and steps away from a sandy private association beach. This is a perfect place to unwind, connect with nature and enjoy time with family and friends.

Vacation rentals for every style

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Popular amenities for Middlesex County vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Middlesex County

Home in East Hampton

4.87 out of 5 average rating, 97 reviews

Beautiful Lake House on Lake Pocotopaug

Home in Colchester

4.89 out of 5 average rating, 19 reviews

Hilltop Hideaway

Cottage in Hebron

4.89 out of 5 average rating, 117 reviews

Welcome to The Holly at Amston Lake

Cottage in Lebanon

4.97 out of 5 average rating, 38 reviews

"The Napping House". Lake front, kayaks, fire pit.

Cabin in East Hampton

4.79 out of 5 average rating, 14 reviews

Spacious family lakeside homestead

Home in Middletown

4.95 out of 5 average rating, 39 reviews

Hot Tub and pool Home away from home

Cottage in Deep River

4.91 out of 5 average rating, 22 reviews

Serene Waterfront Cottage

Cottage in Old Saybrook

4.95 out of 5 average rating, 39 reviews

Little cottage of gratitude

Destinations to explore