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Vacation rentals in Chester

Vacation rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

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

  • Stunning Artisan Waterfall Escape, Walk Downtown
    SUPERHOSTEntire house · 6 guests · 3 beds · 3 bathrooms
    Stunning Artisan Waterfall Escape, Walk Downtown

    Over ten years of craftsmanship went into creating a work of art using more than 80% recycled building 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 gas fire place. If you are looking for a place to get away from it all, look no further!

    What guests are saying:

    “This is a must stay! This house is a surprise in every room. It’s unique, interesting, rustic, and peaceful. Each level offers a different kind of stay. If you’re seeking a private retreat the downstairs is the place to be with an easy access to the amazing yard in the back with chairs overlooking the waterfall. We often used the main level to cook and play games on the deck. Upstairs offers amazing views of the waterfall as well as the yard. The town of Chester is small, a nice getaway from the noisy city. There’s a Sunday market throughout the summer months, which our neighbors told us about. The neighbors are super friendly too! All around we had an amazing stay and plan on coming back in the future.”

  • Bungalow on the pond
    SUPERHOSTEntire bungalow · 2 guests · 1 bed · 1 bathroom
    Bungalow on the pond

    Fishing blackhall pond... boat... kayak.. canoe on premises...great setting.. sunsets...quiet... peaceful slice of heaven. No extra charge for the Bullfrog!!!

    What guests are saying:

    “June bungalow was AMAZING ! Not a single thing wrong about this place, she greeted is with a delicious loaf of banana bread, fully stocked essentials for breakfast.. tv and wifi, and the best view to wake up to every morning. The hill was a little steep so low cars should be careful, but other than that such an extraordinary place. We will be more than happy to come back !”

  • Unique, fun riverfront cottage
    Entire house · 4 guests · 4 beds · 1 bathroom
    Unique, fun riverfront cottage

    Our guesthouse is on the Connecticut River in the treasured small town of Chester, half-way between New York and Boston – a little over two hours from each city and 45 minutes from New Haven and Hartford. The cottage features a wide porch, private front yard overlooking the river; a living room with a couch that pulls out to sleeps two comfortably, a dining area and kitchen at one end with a dishwasher. There's a bedroom with a queen-sized bed and a good-sized bathroom with tub and shower. The house, on our four-acre property, is private and quiet and about two miles from the center of the village which is well-appointed with wonderful restaurants, a professional theater, galleries and one-of-a-kind shops. There is endless hiking and kayaking possibilities with a boat launch ramp adjacent to the property. Theater, music and a variety of activities and things to do are all close by. The cottage is $130 a night; $700 a week or $2000 a month. During January and February, 20209, the price is $110 a night; $660 a week and $1700 a month. We’d love to have you stay.

    What guests are saying:

    “I almost hesitate in offering this review -- as I would rather Claudia's Unique, Fun Cottage be kept secret! Yet good, transcendent human achievements do not remain secret. Claudia's Cottage is the alchemy of Perfect spatial design, decoration, and fundamental amenities; every little and big thing have been considered, thought through, and tuned for guests' comfort and pleasure. Sunrise over the Connecticut River through the virtually floor-to-celing glass east wall is magnificent. The cottage is equipped with The Best of everything you might need for for any tenable wish or whim. The location is private, yet convenient to the delightful Chester Village a mellow mile or two south. The architecture -- it is not so small a structure as the photos might suggest -- lives up to a genius vision of setting, scale, and proportion. There is motion-sensitive lighting to illuminate your way returning after dark, parking with extravagant turnaround space, and responsive mechanicals (central heating, well-pressured hot and cold running water, inspired lighting, abundant electrical outlets). I (we — Katharine and I) have returned time after time to find subtle improvements to the overall space, yet the essential romantic charm prevails. Stay for the peace and tranquility, and for the diverse recreational and arts opportunities nearby. Leave with a refreshed spirit. Claudia's visionary Unique Fun Guest Cottage is a priceless experience. Bring your best and highest hopes and dreams.”

Holiday rentals for every style

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Popular amenities for Chester holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester

Convenient and Cute in Downtown Old Saybrook
SUPERHOSTEntire flat
Convenient and Cute in Downtown Old Saybrook
Price:€99 / night
Chester Village 'Pied-à-terre' above art gallery
SUPERHOSTEntire flat
Chester Village 'Pied-à-terre' above art gallery
Price:€114 / night
The Gardener's Cottage
Entire guest house
The Gardener's Cottage
Price:€106 / night
Beautiful Essex - Wonderful for holiday fun! 175B
SUPERHOSTEntire house
Beautiful Essex - Wonderful for holiday fun! 175B
Price:€75 / night
Quiet setting for this guesthouse with pool.
SUPERHOSTEntire guest house
Quiet setting for this guesthouse with pool.
Price:€155 / night
Annie's Place. Cottage on Horse/Animal/Rescue Farm
SUPERHOSTEntire cabin
Annie's Place. Cottage on Horse/Animal/Rescue Farm
Price:€119 / night
Large En Suite, Private Entrance & Bath, King Bed
SUPERHOSTPrivate room
Large En Suite, Private Entrance & Bath, King Bed
Price:€72 / night
Charming Chester Retreat- Walk to Town Center!
SUPERHOSTEntire guest suite
Charming Chester Retreat- Walk to Town Center!
Price:€140 / night
The Green Room at Cold Spring Farm
SUPERHOSTPrivate room
The Green Room at Cold Spring Farm
Price:€40 / night
Unique apartment, former contemporary art gallery.
SUPERHOSTEntire loft
Unique apartment, former contemporary art gallery.
Price:€110 / night
Private entrance guest suite in Lovely Rural Area
SUPERHOSTEntire guest suite
Private entrance guest suite in Lovely Rural Area
Price:€49 / night
Waterside Beach Retreat
SUPERHOSTEntire house
Waterside Beach Retreat
Price:€211 / night
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