Places to stay in Killingworth

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Top-rated places to stay in Killingworth

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Guest favorite

A gravel path winds through a lush green landscape, flanked by trees offering shade. A black fence runs alongside the pathway, with the area around it appearing well-maintained. A checkered blanket is draped over the fence, adding a touch of color to the natural setting.

Apartment in Killingworth

4.9 out of 5 average rating, 48 reviews

Life on the Farm

Imagine living on a horse farm! Enjoy the wildlife, & watch horses graze right from your steps. Relax, at this unique tiny getaway. As you drive down the entry to Fortunato Farm, you’ll feel a level of comfort allowing relaxation. Open the door, sip your coffee in the sunshine. You're in the country, yet close to CT shoreline areas & restaurants, Clinton Town Beach, and only 15 minutes to Middletown. 25 Miles to Tweed Airport and 45 Miles to Bradley International. 37 miles to Mystic & Mohegan

Guest favorite

The kitchen area includes a sleek granite countertop with two wire-frame stools positioned underneath. Natural light enters through the adjoining living space, highlighting the warm wooden flooring. Sliding glass doors lead to a bright living room, creating a sense of openness and connection.

Apartment in Chester

4.93 out of 5 average rating, 371 reviews

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

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/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, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

Guest favorite

A striking lake scene captures a vibrant sunset, with vivid hues of red and purple reflected on the calm water. The surrounding shoreline is lined with trees silhouetted against the colorful sky, offering a serene and picturesque view.

Home in East Haddam

4.95 out of 5 average rating, 222 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.

Guest favorite

A sandy beach stretches along the water's edge, with individuals walking near the shoreline. A small boat can be seen in the distance, alongside calm waves lapping gently against the sand. Several trees and structures are visible along the waterfront, contributing to a serene coastal atmosphere.

Cottage in Westbrook

4.89 out of 5 average rating, 160 reviews

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.

Superhost

A fenced area features a group of chickens, varying in color and size, foraging on the ground. In the background, a quaint shed with large windows stands under dappled sunlight, surrounded by greenery, suggesting a serene outdoor environment.

Home in Westbrook

4.79 out of 5 average rating, 125 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 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

4.94 out of 5 average rating, 143 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views of River. Convenient to beaches, and includes free pass to the Clinton Town Beach! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to groceries, coffee shops and amazing CT scenery! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants with music, and lots more.

Guest favorite

An outdoor space is presented featuring a gravel area surrounded by comfortable blue Adirondack chairs. A fire pit is centrally located, and a wooden deck can be seen in the background, furnished with a dining set and shaded by a bright yellow umbrella.

Cottage in Chester

4.97 out of 5 average rating, 273 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 favorite

A young piglet is seen resting on a bed of straw. Its shiny black and white fur contrasts with the golden straw, while its small ears perk up. The background features blurred earthy tones, suggesting a rustic farm environment.

Guesthouse in Portland

5 out of 5 average rating, 200 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Top guest favorite

Home in Haddam

5 out of 5 average rating, 126 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 favorite

A detailed map indicates three public parking lots and key streets in Downtown Chester. Lot #1 is located on Water Street, Lot #2 at the Cemetery, and Lot #3 on Maple Street. Sidewalks are highlighted for ease of access into the downtown area.

Loft in Chester

4.99 out of 5 average rating, 142 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.

Guest favorite

A serene outdoor space features a gravel pathway bordered by lush greenery and decorative rocks. A chair is positioned on the path, offering a quiet spot for relaxation. Ferns and hostas complement the natural setting, enhancing the connection to the surrounding trees.

Loft in Killingworth

4.93 out of 5 average rating, 60 reviews

A Peaceful Perch

Rustic, Restful and away from activity but under 10 minutes to the shoreline. You may find this over the garage studio the perfect place to perch for a weekend or a week. A short drive to the charming little town of Madison with many good restaurants and shops and to Hammonasset State park with walking trails and a beautiful beach . 48 River Rd. Is situated on the edge of a glacial rock formation on a scenic country road and is accessible to all the Good Stuff.

Guest favorite

A mirrored closet showcases organized shelves with neatly folded blankets and linens. A drawer unit is positioned below the shelving, providing additional storage. Soft natural light filters through a nearby window, illuminating the wood flooring and creating a bright atmosphere in the space.

Guesthouse in Clinton

4.94 out of 5 average rating, 231 reviews

The Gardener's Cottage Dog friendly/weekly/monthly

The Gardener's Cottage, less then a mile from the Long Island Sound, is a great alternative to the common hotel. Situated a stones throw from Hammonasset State Park and Beach, Clinton Outlets, and the Shore Line East train station. Near by you will find places to kayak, Chamard Wineries, Marinas and many quaint New England towns. The Cottage is fitted with it's own router coupled with an eating nook that can double as a work space. Pets are allowed. Self check-in

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Popular amenities for Killingworth places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Killingworth

Guest favorite

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

4.97 out of 5 average rating, 34 reviews

Adorable Beach House on LI Sound

JessieRating, 5 stars6 days ago

Such a beautiful place! So much to walk to and had great views of the ocean. Very clean and tidy space with everything you would need! Eileen was very responsive and super friendly. Defiantly coming back!

An open interior space features a circular design with wooden beams converging at a skylight. Comfortable seating areas include two sofas and multiple chairs, complemented by a dining table. The warm wooden flooring enhances the inviting atmosphere, with natural light filtering through the windows.

Yurt in Guilford

4.86 out of 5 average rating, 124 reviews

Hartwoods Yurt

AlexRating, 5 stars2 weeks ago

We stay here often, and always find something new to appreciate. It's been a chilly spring, but thankfully, the wood stove kept us all cozy. Being up in the trees, we could hear so many unique birds! We usually cook, but found the local restaurants in Guilford to be quite good. I say it every time, but it's always the getaway my family needs with the right amount of nature to escape, without sacrificing too many creature comforts. It's our happy place!

Top guest favorite

A large two-story house features a dark exterior with stone accents and multiple gabled roofs. Large windows allow ample natural light to enter, while a wooden front door adds a welcoming touch. Lush greenery surrounds the property, enhancing its natural setting.

Apartment in Branford

5 out of 5 average rating, 30 reviews

Stedley Creek

LorettaRating, 5 stars3 weeks ago

Selestria was super kind & supportive! She made us feel welcomed and made herself available for calls if needed. The home was clean and nice looking :)

Guest favorite

A spacious living area showcases exposed wooden beams and a stone fireplace. A cozy sofa and low coffee table are positioned on a textured rug. Natural light enters through multiple windows, illuminating the open space that leads to the kitchen.

Home in Haddam

4.97 out of 5 average rating, 29 reviews

The Farmhouse Stay

MarisaRating, 5 stars2 weeks ago

Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!

Guest favorite

A modern kitchen showcases a sleek stovetop and a knife block on the counter. In the background, an open-concept living and dining area is visible, featuring large windows that offer views of the Connecticut River and abundant natural light.

Home in East Hampton

5 out of 5 average rating, 19 reviews

CT River Retreat - Modern Home with CT River Views

BrianaRating, 5 stars1 week ago

We had an amazing stay at Peter’s home by Saint Clement’s Castle for our wedding weekend! From start to finish, Peter was an exceptional host—friendly, responsive, and incredibly flexible with the details of our stay, which helped make a busy and emotional weekend so much smoother. The home itself was spotless, modern, and thoughtfully maintained. Every room felt comfortable and inviting, and the clean, updated aesthetic made it the perfect place to relax between events and get ready for our big day. It truly felt like a peaceful retreat during a very special time in our lives. We couldn’t have asked for a better experience and would absolutely recommend Peter’s place to anyone visiting the area—especially for events at Saint Clement’s. Thank you again, Peter!

Top guest favorite

Home in Westbrook

5 out of 5 average rating, 63 reviews

Home Away From Home

ColeenRating, 5 stars2 weeks ago

We had a great stay. Lots of space for our family. Highly recommend this property and host.

Top guest favorite

A sunlit room features large windows that provide unobstructed views of the surrounding landscape. A colorful area rug adds warmth to the tile floor, while the vaulted ceiling enhances the spacious feeling. Natural light streams in, creating a bright, inviting atmosphere.

Home in Haddam

4.95 out of 5 average rating, 22 reviews

Luxe Lake House Retreat Between Boston & New York

DelphineRating, 5 stars2 weeks ago

The place is so peaceful and gorgeous, almost like being in a nature preserve but not far from anything either. We saw deer, a fox, a heron, and lots of adorable chipmunks. It was the perfect place to stay during a graduation weekend where the town was bustling and we needed a place to decompress when not on campus. The lawn is simply stunning, and there are incredible views on the the pond and the sky from pretty much every room in the house. We were there during a wet spring and everything was green and fresh. It must be spectacular in the fall or during a snowy winter. Shawn is a super kind, attentive host. We hope to come back in 3 years for our next graduation! Thank you for letting us stay here!

Superhost

Cabin in Haddam

4.9 out of 5 average rating, 67 reviews

The Off-Grid Cabin on Turkey Hill

SydneyRating, 5 stars2 weeks ago

Had a great time at the cabin. Felt right in the middle of nature. The surrounding area was very loud though with people riding around on 4 wheelers. The host was very responsive and helpful. Make sure you pack your own water and plenty of things to provide light.

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Places to stay in Killingworth

Top-rated places to stay in Killingworth

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