Holiday rentals in Killingworth

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Top-rated holiday rentals in Killingworth

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

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Top guest favourite
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.
Cottage in Guilford
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”.

Top guest favourite
A peaceful view of Paper Goods Pond is captured, showcasing calm waters reflecting the sky. Surrounding trees display vibrant autumn colors, and a grassy area leads down to the water's edge. The serene landscape provides a backdrop for relaxation and connection with nature.
Flat in Berlin
4.91 out of 5 average rating, 110 reviews

Pond View Retreat I in Central CT

Comfortable 1 bedroom apt. Centrally located between Hartford and New Haven Near CCSU, UCONN Medical, HOCC, Hartford, Middletown. Perfect for extended stay. Business, nurses, snowbirds. We host short term if available close to requested dates. Separate one bedroom apts. 2nd floor. Washer/Dryer. See our 2nd listing Pond View Retreat II. Clean, safe location. Close to train station, banks, restaurants, grocery stores ,hwy. Relax and enjoy the four seasons over looking Paper Goods Pond!

Top guest favourite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam
4.93 out of 5 average rating, 298 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! 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 the Mohegan Casino.

Top guest favourite
A modern living space features a comfortable sofa, a circular coffee table, and a television unit. Large sliding glass doors create a seamless view of the outdoors, with natural greenery visible beyond the private deck. Soft natural light fills the room, enhancing its inviting ambiance.
Guest house in Guilford
4.99 out of 5 average rating, 512 reviews

Get Back to Nature at a Modern Wood Clad Getaway

HAPPY SPRING… PEEPERS are singing. The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Guest favourite
A serene outdoor space is presented, featuring two black adirondack chairs positioned on a well-maintained lawn. Colorful flower pots are placed on either side of a small table, with lush greenery surrounding the area and a tranquil lake visible in the background.
Home in Westbrook
4.8 out of 5 average rating, 138 reviews

The Dragon Fly Garden

The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Guest favourite
The red yurt is set among tall trees, showcasing a spacious wooden deck surrounded by a lattice railing. Large windows allow natural light to enter, while the soft curves of the yurt blend harmoniously into the wooded landscape.
Yurt in Guilford
4.87 out of 5 average rating, 143 reviews

Hartwoods Yurt

Enjoy a unique wilderness getaway and unwind in a peaceful, 10.3 acre wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

Guest favourite
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
4.97 out of 5 average rating, 299 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.

Top guest favourite
An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.
Cottage in Guilford
4.99 out of 5 average rating, 107 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.

Top guest favourite
An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.
Home in Haddam
4.99 out of 5 average rating, 149 reviews

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

Top guest favourite
The charming barn exterior is illuminated by warm string lights, highlighting its rustic wood finish. Adirondack chairs are arranged in the lush, level yard, inviting relaxation. A covered porch extends from the barn, enhances outdoor living space while offering a cozy atmosphere as twilight approaches.
Barn in Essex
4.96 out of 5 average rating, 182 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Guest favourite
The exterior of Lori Warner Studio/Gallery showcases a vibrant red door framed by large glass windows. A deep blue awning offers shade, while decorative planters with greenery are positioned beside the entrance. Outdoor seating is visible in the background, complementing the inviting atmosphere.
Flat in Chester
4.92 out of 5 average rating, 415 reviews

Chester Village 'Pied-à-terre' above art gallery

Our lovely apartment is well designed in an ideal location. A sunshine filled living room w/high ceilings, a private bedroom in back, and large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique. We're neighbor to some of the BEST restaurants, art and shopping in CT! We know you'll enjoy your stay!

Top guest favourite
An open studio layout is presented with soft blue walls and modern lighting. A cozy couch is positioned near large windows, while a kitchen featuring white cabinetry is visible in the background. Natural light enhances the airy feel of the space.
Guest suite in Essex
4.97 out of 5 average rating, 124 reviews

The Nest

Our warm and inviting studio apartment with bright and cheery decor offers a cozy get away any time of year. Nestled in a peaceful country neighborhood with endless hiking trails, beaches, and cozy villages nearby. The Nest offers a comfortable and convenient place to stay while enjoying the surrounding area.

Popular amenities for Killingworth holiday rentals