Holiday houses in Essex

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Essex

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

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Guest favourite

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.

22–29 Aug

$723 NZD per night

Guest favourite

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!

13–20 Jan

$388 NZD per night

Guest favourite

Home in Essex

4.97 out of 5 average rating, 33 reviews

Ideal Historic Home in Essex Village

Welcome to your opportunity to live the village life and stay in the heart of Essex Village. This is the first time a vacation rental home on Main St in Essex, CT has been listed on Airbnb. Chosen as the best small town in America by Norman Crampton in his book, The 100 Best Small Towns in America. Essex also appears in 1000 Places to Visit Before You Die. Located on the Connecticut River, this friendly New England community has been welcoming travelers since before the American Revolution.

4–11 Jan

$895 NZD per night

Guest favourite

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.

30 Oct – 6 Nov

$645 NZD per night

Guest favourite

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.

13–20 Feb

$305 NZD per night

Guest favourite

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.

12–19 Jan

$442 NZD per night

Guest favourite

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

6–13 Jun

$437 NZD per night

Guest favourite

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.

21–28 Nov

$348 NZD per night

Guest favourite

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.

30 Oct – 6 Nov

$660 NZD per night

Guest favourite

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.

10–17 Nov

$197 NZD per night

Guest favourite

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.

23–30 Jul

$1,422 NZD per night

Guest favourite

Apartment in Deep River

4.82 out of 5 average rating, 171 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.

7–14 Jan

$232 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Essex holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

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 holiday rentals in Essex

Guest favourite

Cottage in Essex

4.94 out of 5 average rating, 36 reviews

Cheerful, private cottage in Essex village.

18–25 Jan

$469 NZD per night

Guest favourite

Loft in Chester

4.99 out of 5 average rating, 84 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

19–26 Apr

$364 NZD per night

Guest favourite

Cottage in Essex

4.93 out of 5 average rating, 30 reviews

Essex House

30 Oct – 6 Nov

$584 NZD per night

Guest favourite

Guesthouse in Chester

5.0 out of 5 average rating, 41 reviews

Delightful Cottage in Charming Chester

19–26 Aug

$458 NZD per night

Guest favourite

Cottage in Deep River

4.89 out of 5 average rating, 19 reviews

Country Cottage in Private Garden Setting

11–18 Mar

$441 NZD per night

Guest favourite

Home in Essex

5.0 out of 5 average rating, 51 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

14–21 Jan

$1,091 NZD per night

Guest favourite

Guesthouse in Essex

5.0 out of 5 average rating, 27 reviews

Adorable 2 bedroom guesthouse in Essex village

16–23 Sep

$660 NZD per night

Guest favourite

Home in Haddam

5.0 out of 5 average rating, 73 reviews

Cozy Comforts!

6–13 Dec

$248 NZD per night

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Quick stats about holiday 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	$186 NZD before taxes and fees

Holiday houses in Essex

Top-rated holiday rentals in Essex

Home in Lyme

Apartment in Chester

Home in Essex

Home in Chester

Home in East Lyme

Cottage in Chester

Apartment in Chester

Apartment in Deep River

Home in Lyme

Apartment in East Haddam

Barn in Essex

Apartment in Deep River

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Essex holiday rentals

Stay near Essex's top sights

Other great holiday rentals in Essex

Cottage in Essex

Loft in Chester

Cottage in Essex

Guesthouse in Chester

Cottage in Deep River

Home in Essex

Guesthouse in Essex

Home in Haddam

Quick stats about holiday rentals in Essex

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore