We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Rental unit in Chester

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!

Cottage in Westbrook

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.

Home in Chester

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 suite in Wallingford

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.

Cottage in Chester

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.

Rental unit in East Lyme

Brand New Direct Lakefront - Panoramic Sunsets

Completely remodeled lakefront apartment offering sweeping views of Pattagansett Lake. Open floor plan, fully equipped kitchen and massive deck make for an ideal gathering place to catch up with family or friends. All three spacious bedrooms offer comfy queen memory foam mattresses, fresh linens and UHD smart TVs. Two full bathrooms, high speed internet and in-unit laundry. Picturesque natural setting yet close to town amenities, restaurants, beaches, casino and area attractions.

Rental unit in Deep River

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.

Cabin in East Haddam

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*.

Home in Lyme

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“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 water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature

Rental unit in East Haddam

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.

Barn in Essex

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.

Rental unit in Deep River

Loft apartment, deck and great water view

Great location, walk to town & only steps to the Connecticut River. Great for train aficionados- you can watch and photograph the famous Essex steam train in action.This historic factory built in 1874 has manufactured sails, metal objects and lastly Lace. Enjoy your private comfortable apartment with river views and deck.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Essex vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Essex's top sights

Essex Steam Train & Riverboat60 locals recommend

Connecticut River Museum38 locals recommend

Scotch Plains Tavern13 locals recommend

Other great vacation rentals in Essex

Home in Westbrook

Family-Friendly Cottage by The Shore

Rental unit in Portland

SUNNY PRIVATE 1 BEDROOM APARTMENT

Rental unit in Chester

Charming Chester Retreat-Hidden Gem

Cottage in Waterford

Coastal Cottage Private Studio

Rental unit in New London

Quiet Neighborhood home close to everything

Home in Lyme

Stunning, peaceful and private home

Rental unit in Norwich

Cozy Stay w Pool 4 mi to Mohegan, 7 mi to Foxwoods

Condo in Middletown

Entire place to yourself Cromwell/Middletown Line

Other great vacation rentals in Essex

Guesthouse in Chester

Delightful Cottage in Charming Chester

Loft in Chester

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Home in Old Saybrook

Steps to Beach! *Cozy Cottage* Pet Friendly

Guest suite in Westbrook

*Newly Renovated* Private Suite - Steps to Beach!

Home in Essex

Hyde House- a newly remodeled Essex Village Home.

Rental unit in Clinton

Cozy Shoreline Getaway

Home in Haddam

Cozy Comforts!

Cottage in Essex

Essex House

Quick stats about vacation rentals in Essex

Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
$110 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Essex?
Yes! Work meets play with ease at over 20 vacation rentals in Essex featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Essex?
Four-legged friends are welcome in Essex. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Essex have wifi?
Absolutely! We offer over 20 house rentals with wifi in Essex. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Essex?
Experience the best of Essex with our house rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Essex have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Essex. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Essex?
Essex has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore