Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 313 reviews

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

If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up 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! NEW! Winter weekdays - ONE night stays are now available - message us!

Jan 13 – 20

G$40,790 GYD per night

Guest favorite

Guesthouse in Chester

5.0 out of 5 average rating, 41 reviews

Delightful Cottage in Charming Chester

Enjoy all the Connecticut River Valley has to offer and use this newly renovated cottage as your relaxing home base. The cottage is a 2 min. drive (or 12 min. walk) to charming downtown Chester. There you will find delicious dining options, unique shops, galleries, a brewery and a theater. Chester is also home to a wonderful Sunday farmers market -mid June to mid October. Area attractions include Gillette Castle, Essex Steam Train, Florence Griswold Museum, CT River Museum and wonderful hiking.

Aug 19 – 26

G$45,430 GYD per night

Guest favorite

Home in Chester

4.98 out of 5 average rating, 195 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.

Oct 30 – Nov 6

G$64,930 GYD per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 496 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

Feb 17 – 24

G$18,243 GYD per night

Guest favorite

Cottage in Chester

4.98 out of 5 average rating, 228 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.

Jan 12 – 19

G$44,405 GYD per night

Guest favorite

Apartment in Chester

4.98 out of 5 average rating, 131 reviews

Charming Chester Retreat-Hidden Gem

This 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

Jun 6 – 13

G$45,366 GYD per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 147 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Welcome! We are sure you will enjoy your stay in this centrally located first-floor apartment, which sleeps 5-6 guests! You'll feel at home in this cozy 2-bedroom unit, stocked with everything you would need during your stay. Walking distance away from Main Street and Wesleyan, you'll be able to explore all Middletown and the surrounding area has to offer. Two porches, a fenced-in backyard, and a firepit are all available for your use! Pets are welcome! Any questions? Message us!

Sep 4 – 11

G$27,012 GYD per night

Guest favorite

Apartment in Deep River

4.91 out of 5 average rating, 104 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.

Nov 21 – 28

G$35,504 GYD per night

Guest favorite

Loft in Chester

4.99 out of 5 average rating, 84 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.

Apr 19 – 26

G$37,470 GYD per night

Superhost

Cabin in East Haddam

4.89 out of 5 average rating, 335 reviews

Getaway Machimoodus - NYC/Boston

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Jul 17 – 24

G$52,674 GYD per night

Guest favorite

Apartment in East Haddam

4.89 out of 5 average rating, 104 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.

Nov 10 – 17

G$21,462 GYD per night

Guest favorite

Barn in Essex

4.98 out of 5 average rating, 124 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.

Jul 23 – 30

G$149,780 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chester's top sights

Gillette Castle State Park83 locals recommend

Cockaponset State Forest9 locals recommend

Gillette Castle7 locals recommend

Red House6 locals recommend

Adams Hometown Market8 locals recommend

Pattaconk 1850 Bar & Grille8 locals recommend

Other great vacation rentals in Chester

Guest favorite

Apartment in Chester

4.92 out of 5 average rating, 39 reviews

Gingerbread Apartment, Walk Downtown

Nov 14 – 21

G$36,654 GYD per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 73 reviews

Cozy Comforts!

Dec 6 – 13

G$22,585 GYD per night

Guest favorite

Apartment in Chester

4.99 out of 5 average rating, 69 reviews

The Millhouse Downtown Chester

May 12 – 19

G$56,652 GYD per night

Guest favorite

Cottage in Deep River

4.89 out of 5 average rating, 19 reviews

Country Cottage in Private Garden Setting

Mar 11 – 18

G$42,733 GYD per night

Guest favorite

Home in Chester

4.98 out of 5 average rating, 50 reviews

Tuscan Villa in Chester

Dec 18 – 25

G$100,747 GYD per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

Mar 27 – Apr 3

G$27,144 GYD per night

Guest favorite

Loft in Westbrook

5.0 out of 5 average rating, 59 reviews

Lovely one bedroom studio with on-site parking.

Mar 16 – 23

G$29,935 GYD per night

Guest favorite

Guesthouse in Madison

4.92 out of 5 average rating, 12 reviews

In-law apartment with Private entrance

Sep 17 – 24

G$25,456 GYD per night

Show all

Quick stats about vacation rentals in Chester

Total rentals	10 properties
Popular amenities	Kitchen, Wifi, and Pool
Wifi availability	10 properties include access to wifi
Family-friendly rentals	10 properties are a good fit for families
Total number of reviews	2K reviews
Nightly prices starting at	G$20,897 GYD before taxes and fees

Vacation rentals in Chester

Top-rated vacation rentals in Chester

Apartment in Chester

Guesthouse in Chester

Home in Chester

Guest suite in Wallingford

Cottage in Chester

Apartment in Chester

Apartment in Middletown

Apartment in Deep River

Loft in Chester

Cabin in East Haddam

Apartment in East Haddam

Barn in Essex

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chester vacation rentals

Stay near Chester's top sights

Other great vacation rentals in Chester

Apartment in Chester

Home in Haddam

Apartment in Chester

Cottage in Deep River

Home in Chester

Apartment in Clinton

Loft in Westbrook

Guesthouse in Madison

Quick stats about vacation rentals in Chester

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore