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.

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Guest favorite

Home in Lyme

4.97 out of 5 average rating, 187 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 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.

Aug 22 – 29

$309 per night

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

$170 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

$269 per night

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Feb 13 – 20

$132 per night

Guest favorite

Cottage in Chester

4.98 out of 5 average rating, 229 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

$184 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

$189 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

$112 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

$152 per night

Superhost

Cabin in East Haddam

4.89 out of 5 average rating, 336 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

$220 per night

Guest favorite

Home in Lyme

4.91 out of 5 average rating, 290 reviews

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

Oct 30 – Nov 6

$284 per night

Guest favorite

Apartment in East Haddam

4.9 out of 5 average rating, 105 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

$90 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

$625 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Essex vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Essex's top sights

Essex Steam Train & Riverboat60 locals recommend

The Griswold Inn49 locals recommend

Ivoryton Playhouse28 locals recommend

Connecticut River Museum38 locals recommend

Scotch Plains Tavern13 locals recommend

Black Seal7 locals recommend

Other great vacation rentals in Essex

Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 124 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Nov 10 – 17

$347 per night

Superhost

Cottage in Clinton

4.88 out of 5 average rating, 392 reviews

Shalom Cottage with beach rights.

Sep 7 – 14

$170 per night

Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 257 reviews

Modern Luxurious CT Country Home

Dec 30 – Jan 6

$356 per night

Superhost

Home in Westbrook

4.86 out of 5 average rating, 134 reviews

Family-Friendly Cottage by The Shore

Jun 25 – Jul 2

$221 per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 496 reviews

Wintergreen Gardens Suite @ William Becroft House

Feb 17 – 24

$77 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

$125 per night

Guest favorite

Home in Essex

4.97 out of 5 average rating, 33 reviews

Ideal Historic Home in Essex Village

Jan 4 – 11

$391 per night

Guest favorite

Cottage in Essex

4.94 out of 5 average rating, 36 reviews

Cheerful, private cottage in Essex village.

Jan 18 – 25

$200 per night

Show all

Other great vacation rentals in Essex

Guest favorite

Guesthouse in Essex

5.0 out of 5 average rating, 27 reviews

Adorable 2 bedroom guesthouse in Essex village

Sep 16 – 23

$287 per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 73 reviews

Cozy Comforts!

Dec 6 – 13

$92 per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

Mar 27 – Apr 3

$113 per night

Guest favorite

Home in Old Saybrook

4.98 out of 5 average rating, 48 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Dec 9 – 16

$129 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

$176 per night

Guest favorite

Cottage in Deep River

5.0 out of 5 average rating, 7 reviews

Serene Waterfront Cottage

Nov 20 – 27

$400 per night

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

Jul 5 – 12

$162 per night

Guest favorite

Apartment in Chester

4.92 out of 5 average rating, 39 reviews

Gingerbread Apartment, Walk Downtown

Nov 14 – 21

$153 per night

Show all

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.

Essex vacation rentals

Top-rated vacation rentals in Essex

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Essex vacation rentals

Stay near Essex's top sights

Other great vacation rentals in Essex

Home in Old Lyme

Cottage in Clinton

Home in Old Lyme

Home in Westbrook

Guest suite in Wallingford

Loft in Westbrook

Home in Essex

Cottage in Essex

Other great vacation rentals in Essex

Guesthouse in Essex

Home in Haddam

Apartment in Clinton

Home in Old Saybrook

Cottage in Deep River

Cottage in Deep River

Guest suite in Old Saybrook

Apartment in Chester

Quick stats about vacation rentals in Essex

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Essex?

Are there pet-friendly vacation rentals in Essex?

Do house rentals in Essex have wifi?

How much does it cost to stay in house rentals in Essex?

Do house rentals in Essex have air conditioning?

Are there family-friendly house rentals in Essex?

Destinations to explore