Cottage holiday rentals in Middletown

4.99 out of 5 average rating, 167 reviews

A jetted swim spa is positioned on a deck overlooking Lake Garda at sunset. The water's surface reflects soft hues of orange and pink, with serene trees framing the view. The spa displays an illuminated edge, enhancing the tranquil atmosphere of the lakeside setting.

Cottage in Burlington

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.

4.94 out of 5 average rating, 291 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”.

4.97 out of 5 average rating, 111 reviews

A dining area features a wooden table surrounded by dark chairs, set with blue and white plates. Large windows allow natural light and provide an expansive view of the lake, where boats can be seen in the distance.

Cottage in Middlefield

Anchors' Away-

Welcome to your private lakefront sanctuary. Have the chance to make memories whether it is by fishing on either of the two docks? or the chance to kayak to explore the lake. Completely renovated with comfort and style in mind, this waterfront getaway offers panoramic lake views and direct water access. Start your mornings with coffee on one of the two private docks watching the sunrise. Unwind each evening on the patio all decked out with restful seating and a chance to watch the fireflys.

4.87 out of 5 average rating, 196 reviews

A riverfront deck is furnished with two lounge chairs and a glass table, surrounded by lush greenery and trees. The view overlooks a calm stretch of the Patchogue River, creating a serene environment for relaxation and enjoyment of nature.

Cottage in Westbrook

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

4.89 out of 5 average rating, 176 reviews

A charming two-bedroom cottage is set amidst greenery, featuring a welcoming front porch with a railing. A stone pathway leads to the entrance, and landscaping is visible around the base of the home. Large windows allow natural light to enhance the inviting exterior.

Cottage in Hebron

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.

4.97 out of 5 average rating, 299 reviews

The front exterior of the cottage is shown, featuring a stone pathway leading to the entrance. An orange front door is framed by white railings. Surrounding greenery and seasonal decor complement the inviting atmosphere of the landscaped yard.

Cottage in Chester

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.

4.87 out of 5 average rating, 162 reviews

The exterior of the cottage is shown, featuring a sloped roof and grey shingles. A front porch is visible, with a flag displayed on one side. Lush green grass and landscaping surround the home, while trees provide a natural backdrop.

Cottage in Lebanon

Go Jump in the Lake!

Our recently renovated 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

4.96 out of 5 average rating, 158 reviews

The spacious loft features a sloped ceiling with exposed beams, accommodating a king-size bed and a cozy sofa. A work table is positioned beside a large window that allows natural light to fill the room. A flat-screen TV is mounted on the opposite wall.

Cottage in Collinsville

The Carriage House Skiing Nearby

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

4.94 out of 5 average rating, 141 reviews

A spacious living area features a large sectional sofa adorned with cushions, offering panoramic lake views through expansive windows. A dining table for two is located nearby, with a small workspace and desk chair positioned to enjoy the serene scenery.

Cottage in Plymouth

Lakefront Cozy Oasis 2BR w/ Stunning Sunset Views

It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits!

4.92 out of 5 average rating, 265 reviews

A single-story cottage is set amidst greenery, showcasing maroon siding and multiple windows. The front yard features a manicured lawn with a few flowerbeds, and a stone pathway leads to the entrance, flanked by tall trees providing shade.

Cottage in Middlefield

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.

4.89 out of 5 average rating, 130 reviews

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

The Blue Heron at Amston Lake

3 BEDROOM Quiet Cottage: ~3 minute walk to the Main Beach at private Amston Lake. ~ Fully stocked open floor plan kitchen. Dining table seats 4 with additional seating on covered patio accessible by sliding door. ~Gas grill ~Large, private backyard with fire pit and hammock. ~Canoe and kayak available ~Adult bicycles (2) available upon request. ~Ping pong table, dart board in basement. ~ Close to Airline Trails, vineyards, breweries, casinos, and parks.

4.96 out of 5 average rating, 101 reviews

A living room features natural light streaming through windows, enhancing the warm wood floors. A brown sofa is paired with a woven lounge chair, and a blue coffee table is centered on a light-patterned rug. Wall-mounted shelves display framed art and decorative items.

Cottage in Old Saybrook

1920’s charming dollhouse near South Cove

Simple, no frills guest cottage near South Cove in Old Saybrook. Drop your kayak /paddle board in at the end of the street, walk to town for dinner or a show at the Katherine Hepburn Theater, or enjoy a day at town beach only 1.5 miles away. This is a shabby chic escape in a friendly, quiet neighborhood. A few quirks but tons of charm! If you are looking to unplug and sit by the fire pit, read a book, and go to the beach, this is the place for you.

Popular amenities for cottage rentals in Middletown

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

4.95 out of 5 average rating, 195 reviews

Luxury cottage by the sea with hot tub and pool

4.95 out of 5 average rating, 19 reviews

A charming guest room features a spacious bed with a white coverlet framed by two wooden posts. Comfortable green chairs are positioned beside a small table, which is adorned with a vase of roses, grapes, and glasses of wine.

Cottage in Norfolk

The Cottage at Blackberry River Inn

4.87 out of 5 average rating, 396 reviews

A charming cottage is enveloped in fresh snow, with soft yellow lights glowing from its windows. The white exterior contrasts with the snow-covered landscape, while trees and bushes, dusted with snow, create a peaceful winter setting.

Cottage in Litchfield

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

4.92 out of 5 average rating, 59 reviews

A private hot tub is nestled within a covered gazebo, offering a serene space for relaxation. Soft lighting enhances the inviting water, while draped curtains provide privacy. The backdrop features a view of the nearby lake and surrounding homes, illuminated by dusk.

Cottage in Plymouth

Lakefront Escape | Hot Tub + Spring Views

An open living space is shown with a spiral staircase leading to an upper level. A comfortable seating area is arranged with a soft couch and armchair. A dining table with wooden chairs is positioned near a large window, while a television is mounted on the wall.

Cottage in Old Lyme

4.79 out of 5 average rating, 256 reviews

Private Beach Cottage

A welcoming entrance features a pathway of gray stone leading to a blue cottage with large windows. Flanking the path are colorful garden beds and a grassy lawn. A set of stairs leads up to the front door, painted a cheerful blue.

Cottage in Fairfield Beach

4.8 out of 5 average rating, 10 reviews

The Lil Nauti Cottage, Steps To Fairfield Beach

4.99 out of 5 average rating, 147 reviews

The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.

Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

Pet-friendly cottage rentals

A bright dining area features a table surrounded by six chairs, with a decorative tablecloth. High ceilings with wooden beams enhance the openness. Large windows provide natural light, and a sideboard adds functional storage. A cozy seating arrangement can be seen in the background.

4.99 out of 5 average rating, 159 reviews

"Red House on the Knoll" at Indian Cove

4.78 out of 5 average rating, 106 reviews

A charming home exterior is lined with vibrant green ivy, surrounded by a lush garden area. A gravel pathway leads to the entrance, and cozy seating arrangements are visible in front of the house. Large windows allow natural light to fill the interior.

Cottage in Old Saybrook

Storybook 2 Bedroom Cottage

4.9 out of 5 average rating, 201 reviews

A cozy living room features a stone fireplace surrounded by purple walls. A wooden table sits at the center, adorned with a decorative bowl. A comfortable sofa and a wooden chair are positioned near the fireplace, complementing the warm ambiance.

Cottage in Windsor

In-law apartment in Farmington River Cottage

4.93 out of 5 average rating, 142 reviews

The exterior of a beach cottage is shown, featuring light-colored siding and blue shutters. A white railing surrounds a small porch, leading to a front door. Lush greenery and a few decorative elements enhance the inviting appearance of the home.

Cottage in Milford

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

4.87 out of 5 average rating, 240 reviews

The exterior of a charming red schoolhouse and accessory building is surrounded by vibrant foliage. A white wooden fence outlines the property, leading to a gravel pathway. The buildings feature classic architectural details, with windows framed in white and a backdrop of lush trees.

Cottage in Granby

The Little Red Schoolhouse ~ Circa 1877

4.94 out of 5 average rating, 376 reviews

A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.

Cottage in Milford

Spring Sale! CozyCottage/Pet-friendly/WalktoBeach

4.96 out of 5 average rating, 113 reviews

A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.

Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

4.96 out of 5 average rating, 260 reviews

The exterior of the cottage is visible, showcasing a light grey facade with white trim. A paved driveway accommodates a parked car. A large tree provides shade, and an American flag hangs near the entrance. A spacious lawn is present, bordered by a fence.

Cottage in Groton

EASY BEAT

Private cottage rentals

4.89 out of 5 average rating, 46 reviews

A welcoming sign for Lake Pocotopaug is displayed prominently, featuring a blue background with white lettering. The lake and autumn-colored trees are visible in the background, providing a serene atmosphere typical of the East Hampton area.

Cottage in East Hampton

Charming 3 bedroom cottage on Lake Pocotopaug

4.91 out of 5 average rating, 67 reviews

The exterior of a charming two-story white house is shown, surrounded by blooming pink and white trees. The driveway leads to a double garage, and neatly manicured bushes frame the home. Soft clouds drift in a blue sky, adding a serene ambiance to the scene.

Cottage in Farmington

Charming Carriage House in Historic Farmington, CT

4.99 out of 5 average rating, 77 reviews

A charming cottage with a white exterior is presented, featuring a spacious front porch and decorative railings. A basketball hoop stands prominently on the gravel driveway, with planters and shrubbery visible in the foreground. Clear blue skies enhance the inviting appearance of the home.

Cottage in Westbrook

Beautiful Updated Cottage walk to the Beach

4.91 out of 5 average rating, 45 reviews

A wooden dining table with several chairs is positioned on the sandy beach, overlooking the water. A vibrant sunset casts warm hues across the sky and reflects on the calm sea. Nearby rocks are visible along the shoreline.

Cottage in Lordship

Waterfront Beach Cottage in Connecticut

4.74 out of 5 average rating, 27 reviews

The image captures a serene lake view, highlighting the calm water reflecting the blue sky and distant hills. A wooden dock is visible in the foreground, with a gentle shoreline leading to lush greenery. The landscape is peaceful, surrounded by trees and residential buildings in the distance.

Cottage in Portland

Lake Cottage Getaway

4.98 out of 5 average rating, 41 reviews

An aerial view depicts a charming residential area near the water, showcasing a blend of green lawns, various homes, and a marina. The surrounding landscape highlights the proximity to the river, with trees and the road leading towards the waterfront.

Cottage in Waterford

Game Room-Mins to Beach&Boardwalk-Walk to Marinas

5 out of 5 average rating, 17 reviews

A serene lake view is framed by lush green trees, with the calm water reflecting the clear blue sky. A private dock extends into the lake, providing access to kayaks and paddle boards. Nearby buildings are visible along the shoreline.

Cottage in Holland

Hamilton Cottage | Cozy Lakefront A-Frame

A serene waterside view is presented from the deck, showcasing the calm waters, dotted with small boats. Rocky shorelines and lush greenery line the opposite bank, under a clear blue sky. A patio area with chairs can be seen below the deck.