Vacation rentals in Deep River

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Top-rated vacation rentals in Deep River

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Top guest favorite

A view of a charming town center is presented, featuring a circular stone garden adorned with shrubs and small trees. Nearby buildings include a café and a retail shop, with light streaming down from a late afternoon sun, casting a warm glow over the scene.

Apartment in Chester

4.98 out of 5 average rating, 167 reviews

Charming Chester Retreat - Cottage

Home away from Home! Thoughtfully designed 2 bed, 1 bath unit is the perfect blend of style and comfort. The space has been re-designed to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! New England getaway / Hidden Gem / Retreat

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 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 red chair is positioned in the corner of a room, surrounded by tall windows that provide ample natural light. The wooden flooring and cozy rug underfoot create a warm setting, while the greenery outside adds a refreshing touch to the view.

Home in Chester

4.98 out of 5 average rating, 210 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

Guest favorite

A refreshing pool is surrounded by lush green grass and trees, creating a serene outdoor setting. A hammock is visible in the background, inviting relaxation. A single foot rests on a soft cushion at the pool's edge, suggesting a moment of leisure.

Tiny home in Deep River

4.71 out of 5 average rating, 7 reviews

Her tiny Parisian boat house

Solo vacation? Reconnect with nature at this unforgettable escape. Or a Perfect work space while lounging by the pool…(in SEASON) this tiny house (on land) has access to an outdoor shower and outdoor soaking tub. Wanna relax? Come Meditate under the giant willow, swing in the hammock or practice yoga. Bathroom (NOT IN THE TINY HOUSE!) is shared and just steps inside the main house with shower and toilet. Great WiFi, front porch to enjoy meals. Bed is a comfytwin with lots of pillows.

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

A comfortable living area features a gray sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, holding books and games. Natural light filters through a nearby window, illuminating the rustic wood-paneled wall and warm-toned floor.

Apartment in Deep River

4.93 out of 5 average rating, 147 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

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.

Top guest favorite

The cottage is depicted from across the tranquil river, showcasing its large glass windows reflecting the warm glow of the interior lights. The surrounding greenery and outdoor dining area create a serene atmosphere, enhancing the peaceful riverside setting.

Home in Lyme

4.98 out of 5 average rating, 270 reviews

“The Answer” Your Unique, Tidal, Riverfront Escape

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil tidal water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

Top guest favorite

The image shows a storage cabinet with two shelves containing a variety of dinnerware. Items visible include plates, bowls, glasses, and mugs. The mugs feature various designs, while the plates are stacked neatly in a row. A clean, neutral backdrop enhances the focus on the organized tableware.

Apartment in East Haddam

4.9 out of 5 average rating, 168 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

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Popular amenities for Deep River vacation rentals

Kitchen

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Deep River

Guest favorite

Barn in Deep River

5 out of 5 average rating, 9 reviews

Salt House

AlisonRating, 5 stars6 days ago

Beautiful and peaceful space with generous and friendly hosts who are nearby to help out. The house is fun, with multiple sources of joy. Definitely the first place where I’ve been supplied with the makings for s’mores. The stairs up to the bedrooms may be tough for a less ambulatory person, so keep that in mind. Also note the earlier than usual checkout time. Neither were an issue for me and I’m likely to stay again if I am in the neighborhood.

Guest favorite

A cozy sleeping area is framed by a large window, offering a view of the serene lake and surrounding nature. Light wood shelving houses decorative items, while a wall-mounted TV is positioned across from a bed adorned with a patterned blanket and decorative pillows.

Tiny home in East Lyme

4.98 out of 5 average rating, 81 reviews

Lakefront Retreat Tiny House

MauriceRating, 5 stars1 week ago

Kevin is doing such a cool thing providing the perfect cozy escape with reasonable cost. Everything was as described and I can’t describe how relaxing and peaceful my stay was, especially considering it was actually a work trip in the area. He was always quick to respond to any needs I had & we had a nice chat after my checkout. Looking forward to hopefully being back in the area to stay at this exact spot again!

Superhost

A light-filled hallway features smooth, polished wooden flooring extending towards open doorways. Neutral-colored walls are complemented by a small decorative plant placed on a white side table. A framed artwork hangs on the wall, adding subtle detail to the space.

Condo in Old Saybrook

4.89 out of 5 average rating, 73 reviews

Seashore getaway - CT shoreline

ScottRating, 5 stars2 weeks ago

Lauren was great and her home was exactly as promised! Great stay and will stay again!

Top guest favorite

Two wooden chairs sit on a stone patio, surrounded by lush green trees. The seating area offers a place to relax and enjoy the natural surroundings, with a gently textured stone floor enhancing the outdoor experience.

Apartment in Clinton

4.99 out of 5 average rating, 69 reviews

Cozy Shoreline Getaway

HowardRating, 5 stars1 month ago

Second time staying at this Airbnb. Excellent hosts, conveniently located, and cottage had all the amenities.

Guest favorite

An outdoor living space is surrounded by lush greenery and vibrant flowers. A patio features seating options including lounge chairs and a dining area under a large umbrella. A manicured lawn enhances the inviting atmosphere, while a fence provides privacy.

Home in Essex Village

4.9 out of 5 average rating, 101 reviews

Historic Essex Home w/ Large Yard Near Downtown!

ChenelRating, 5 stars2 weeks ago

Amazing host , very responsive and proactive

Guest favorite

Place to stay in East Haddam

5 out of 5 average rating, 11 reviews

Charming garden cottage

AmandaRating, 5 stars2 months ago

From the booking, checking in, instructions, to check out everything was perfect! Beautiful views even in the gray weather, comfortable cottage, and unique added touches. Loved all the details and the instructions were easily laid out . We will certainly be back !!

Superhost