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Essex vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Essex

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

Rental unit in Essex
NEW! Downtown Essex Apartment - Steps to River!
Embrace the essence of small-town living at this renovated apartment in Essex, Connecticut. With all the character and charm of a historic home, this 1-bedroom, 2-bathroom vacation rental is perfect for couples and small groups to enjoy a quiet stay by the Connecticut River. Filled with ornate details, this converted unit now boasts modern comforts like WiFi and Smart TVs. Climb up to the widow’s walk to enjoy a view of the water or relax on the patio for a peaceful evening under the stars.
$166 per night
Home in Essex
Historic Essex Home w/ Large Yard Near Downtown!
Brimming with small-town charm, Essex should be the next stop on your bucket list! This inviting 2-bedroom, 1.5-bathroom vacation rental is loaded with country charm as well as a fully equipped kitchen and outdoor living space, making it the perfect home base for your next coastal getaway. Spend your days riding the famous steam train or hiking the scenic trails at a nearby state park, followed by evenings exploring the abundance of local shops, eateries, and attractions that make up Essex.
$204 per night
Barn in Essex
Renovated 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.
$398 per night

Stay near Essex's top sights

Photo of Essex Steam Train & Riverboat
Essex Steam Train & Riverboat60 locals recommend
Photo of Essex Steam Train
Essex Steam Train38 locals recommend
Photo of The Griswold Inn
The Griswold Inn49 locals recommend
Photo of Connecticut River Museum
Connecticut River Museum38 locals recommend
Photo of Scotch Plains Tavern
Scotch Plains Tavern13 locals recommend
Photo of Black Seal
Black Seal7 locals recommend

Other great vacation rentals in Essex

Cottage in Essex
Essex House
$275 per night
Rental unit in Essex
Cozy Essex Getaway
$125 per night
Guesthouse in Essex
Adorable 2 bedroom guesthouse in Essex village
$175 per night
Cottage in Essex
Cheerful, private cottage in Essex village.
$204 per night
Home in Essex
Ideal Historic Home in Essex Village
$381 per night
Home in Essex
Hyde House- a newly remodeled Essex Village Home.
$263 per night
Home in Essex
The Cozy Nook
$106 per night
Loft in Essex
Unique apartment, former contemporary art gallery.
$156 per night
Cottage in Old Saybrook
Storybook 2 Bedroom Cottage
$211 per night
Rental unit in Chester
Chester Village 'Pied-à-terre' above art gallery
$155 per night
Private room in Chester
Comfy Artist View at Chester Village
$122 per night
Guest suite in Chester
Charming Chester Retreat- Near Village Center
$195 per night
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