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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Guest favorite

A private deck features a railing overlooking calm waters, framed by green grass and bordered by trees. Sunlight reflects off the water under a clear blue sky, creating a peaceful view of the surrounding shoreline and distant houses.

Guesthouse in Essex

4.82 out of 5 average rating, 28 reviews

Privateers Boathouse (Village Waterfront)

Right in the middle of all Essex Village offers: shopping, dining, boating. Short drive to beaches, farmstands, golf, hikes, theatre, colleges & more. Very special little waterfront cottage with unrivaled views, private deck & access to town. Park your car once and enjoy all the wonders of Essex Village by foot during your visit. 🌟 Secluded, yet utterly central Village location. 🛶 Access to swimming pool WITH ARRANGEMENT (2 towels provided) 🚣‍♀️ No proper launch for kayak/SUP- but several close

Top guest favorite

An open-concept living area features a well-equipped kitchen with modern appliances and an island with seating. Neutral walls and wooden flooring create a warm ambiance. Two pendant lights hang above the kitchen island, illuminating the space and connecting seamlessly to the dining and living areas.

Home in Guilford

5 out of 5 average rating, 12 reviews

Coastal Getaway

Welcome to your perfect getaway! Nestled in a picturesque coastal town in CT, this newly renovated gem offers a cozy and comfortable retreat with all the modern amenities you need for a memorable stay. Minutes away from sandy beaches where you can soak up the sun or take a leisurely stroll along the shore. The town is known for its dining options, with a variety of restaurants serving everything from fresh seafood to cozy bistros. Enjoy charming boutiques, apple picking & local farmers markets.

Guest favorite

A scenic beach scene captures individuals enjoying a relaxing day by the water. Sun loungers are positioned in the soft sand, with gentle waves lapping at the shore and a vibrant blue sky filled with fluffy white clouds.

Cottage in Guilford

4.93 out of 5 average rating, 267 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

A rustic seafood shack features a prominent sign reading 'Lobster Landing'. The white facade is complemented by red accents, and outdoor seating is visible alongside a wooden fence. Clear skies and a few scattered clouds enhance the setting's open, inviting feel.

Home in Clinton

4.93 out of 5 average rating, 135 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 in any season! The well-equipped, intimate 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. Other favorites include Chamard Vineyard, Shopping Outlets, Essex Steam Train, fantastic Restaurants with music, and lots more!

Top guest favorite

Home in Old Saybrook

5 out of 5 average rating, 49 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.

Guest favorite

A serene lakeside view is captured at sunset, reflecting vibrant colors across the calm water. The shoreline features rocks and grassy areas, with trees framing the scene. A wooden chair is positioned nearby, inviting relaxation while enjoying the natural beauty.

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.

Superhost

A bright and open living area features high ceilings with exposed beams. Large windows allow natural light to fill the space. A comfortable seating arrangement is positioned around a light rug, complemented by modern furnishings. A stylish dining table is set nearby, adorned with fresh flowers.

Cottage in Clinton

4.82 out of 5 average rating, 39 reviews

The Beach Nest-Lux Cottage Steps to the Beach

Come enjoy the cutest cottage on Shore Rd. Newly renovated. Just steps to the beach and minutes away from town and all of the CT shoreline attractions. This newly renovated cottage has all the modern amenities of today and all the old charm of yesterday. The cottage features water views, a fully equipped kitchen, washer/dryer, and dishwasher. The cottage sleeps up to 6 (1 queen,1 bunkbed, and 1 sleeper sofa)and has parking for 2 cars.

Guest favorite

A spacious deck is shown, featuring wicker furniture arranged around a wooden table. The area is bathed in sunlight, with a clear blue sky and visible clouds overhead. A view of neighboring houses and a flagpole adds context to the setting.

Apartment in Madison

4.91 out of 5 average rating, 11 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.

Guest favorite

A screened-in porch offers views of the water and sandy beach, with natural light filtering through large windows. A patterned rug covers the floor, while a white wicker chair invites relaxation. The lush green lawn and shoreline are visible outside.

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.

Guest favorite

A charming home showcases a private deck adorned with planters and ample seating under a striped umbrella. Lush greenery surrounds the area, complementing the shingle-style exterior, and large windows invite natural light into the space.

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.

Top guest favorite

A serene outdoor seating area is displayed, featuring cushioned wicker furniture arranged around a light-colored table. The lush green lawn leads to calm waterfront views, with distant trees and a dock visible across the water under a clear blue sky.

Cottage in Old Saybrook

5 out of 5 average rating, 98 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.

Guest favorite

The tranquil lake reflects a vibrant sunset of pink, orange, and purple hues. Silhouettes of trees frame the scene, while wooden docks extend into the water, enhancing the calming atmosphere of the serene landscape.

Cottage in Hebron

4.92 out of 5 average rating, 105 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.