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, 189 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.

May 5 – 12

ﺩ.ﺇ1,049 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!

Apr 15 – 22

ﺩ.ﺇ725 per night

Guest favorite

Home in Chester

4.98 out of 5 average rating, 196 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.

Jan 26 – Feb 2

ﺩ.ﺇ1,258 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.

Dec 1 – 8

ﺩ.ﺇ780 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

ﺩ.ﺇ767 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 3 – 10

ﺩ.ﺇ475 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.

Dec 28 – Jan 4

ﺩ.ﺇ634 per night

Guest favorite

Apartment in East Haddam

4.89 out of 5 average rating, 106 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.

Oct 13 – 20

ﺩ.ﺇ377 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.

Aug 8 – 15

ﺩ.ﺇ2,632 per night

Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 257 reviews

Modern Luxurious CT Country Home

Beautiful mid-century modern glass and wood house in the forest, featuring tranquil designer spaces and continuously updated amenities. With only 2 hours from New York City and Boston, by train or by car, this is the ideal sanctuary for a perfect getaway. Minimum 2 nights during fall through spring months, 3 to 5-nights minimum in the summer months.

Oct 15 – 22

ﺩ.ﺇ1,504 per night

Guest favorite

Apartment in Deep River

4.83 out of 5 average rating, 172 reviews

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.

Jan 23 – 30

ﺩ.ﺇ423 per night

Superhost

Home in Westbrook

4.86 out of 5 average rating, 134 reviews

Family-Friendly Cottage by The Shore

Whether you’re simply traveling to the area or planning your next vacation, you’ve found the right place. Leave your worries behind and come enjoy our freshly updated home by the shore. With a clean, comfortable and convenient spot to stay you are free to explore & relax.

Oct 10 – 17

ﺩ.ﺇ635 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, 126 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Apr 11 – 18

ﺩ.ﺇ1,447 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

Mar 1 – 8

ﺩ.ﺇ558 per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 500 reviews

Wintergreen Gardens Suite @ William Becroft House

Aug 6 – 13

ﺩ.ﺇ321 per night

Guest favorite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

May 8 – 15

ﺩ.ﺇ550 per night

Guest favorite

Tiny home in Guilford

4.94 out of 5 average rating, 203 reviews

Stay in a Tiny House on a Small Sustainable Farm

Aug 26 – Sep 2

ﺩ.ﺇ647 per night

Guest favorite

Home in Lyme

4.91 out of 5 average rating, 291 reviews

Stunning, peaceful and private home

Dec 5 – 12

ﺩ.ﺇ1,165 per night

Guest favorite

Cottage in Westbrook

4.86 out of 5 average rating, 94 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

Oct 13 – 20

ﺩ.ﺇ500 per night

Guest favorite

Loft in Chester

4.99 out of 5 average rating, 85 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Nov 2 – 9

ﺩ.ﺇ658 per night

Show all

Other great vacation rentals in Essex

Guest favorite

Cottage in Essex

4.93 out of 5 average rating, 30 reviews

Essex House

Nov 7 – 14

ﺩ.ﺇ1,081 per night

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

May 6 – 13

ﺩ.ﺇ575 per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

Mar 5 – 12

ﺩ.ﺇ477 per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 77 reviews

Cozy Comforts!

Dec 14 – 21

ﺩ.ﺇ387 per night

Guest favorite

Home in Essex

5.0 out of 5 average rating, 52 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

Feb 6 – 13

ﺩ.ﺇ1,980 per night

Guest favorite

Apartment in Old Lyme

5.0 out of 5 average rating, 12 reviews

Modern, equipped apt with sauna

May 12 – 19

ﺩ.ﺇ396 per night

Guest favorite

Guesthouse in Madison

5.0 out of 5 average rating, 58 reviews

The Barn by the Sound

Dec 17 – 24

ﺩ.ﺇ608 per night

Guest favorite

Apartment in Chester

4.92 out of 5 average rating, 39 reviews

Gingerbread Apartment, Walk Downtown

Jul 31 – Aug 7

ﺩ.ﺇ581 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
ﺩ.ﺇ404 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

Home in East Lyme

Guest suite in Wallingford

Guest suite in New Haven

Tiny home in Guilford

Home in Lyme

Cottage in Westbrook

Loft in Chester

Other great vacation rentals in Essex

Cottage in Essex

Guest suite in Old Saybrook

Apartment in Clinton

Home in Haddam

Home in Essex

Apartment in Old Lyme

Guesthouse in Madison

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