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.

Jul 26 – Aug 2

R7,752 ZAR 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!

Nov 13 – 20

R3,784 ZAR 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.

Mar 12 – 19

R6,511 ZAR 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.

Jan 26 – Feb 2

R2,886 ZAR 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.

Mar 13 – 20

R4,039 ZAR 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

R4,056 ZAR 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 4 – 11

R3,287 ZAR 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 20 – 27

R6,030 ZAR 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.

Mar 6 – 13

R1,952 ZAR 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 30 – Aug 6

R13,624 ZAR per night

Guest favorite

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.

Jan 9 – 16

R2,176 ZAR 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.

Sep 13 – 20

R3,602 ZAR 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

Superhost

Cabin in East Haddam

4.89 out of 5 average rating, 336 reviews

Getaway Machimoodus - NYC/Boston

Jul 19 – 26

R4,791 ZAR per night

Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 257 reviews

Modern Luxurious CT Country Home

Jan 1 – 8

R7,785 ZAR per night

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 12 – 19

R7,577 ZAR per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 147 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Sep 3 – 10

R2,457 ZAR per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 498 reviews

Wintergreen Gardens Suite @ William Becroft House

Feb 9 – 16

R1,659 ZAR per night

Guest favorite

Tiny home in Guilford

4.94 out of 5 average rating, 202 reviews

Stay in a Tiny House on a Small Sustainable Farm

Aug 21 – 28

R3,291 ZAR per night

Guest favorite

Home in Essex

4.97 out of 5 average rating, 33 reviews

Ideal Historic Home in Essex Village

Dec 7 – 14

R8,532 ZAR per night

Guest favorite

Loft in Westbrook

5.0 out of 5 average rating, 59 reviews

Lovely one bedroom studio with on-site parking.

Sep 30 – Oct 7

R2,723 ZAR 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

Dec 2 – 9

R6,382 ZAR per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 73 reviews

Cozy Comforts!

Jan 4 – 11

R2,024 ZAR per night

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

May 28 – Jun 4

R2,929 ZAR per night

Guest favorite

Home in Essex

5.0 out of 5 average rating, 51 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

Dec 24 – 31

R12,526 ZAR per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

Jan 5 – 12

R2,469 ZAR per night

Guest favorite

Home in Old Saybrook

4.98 out of 5 average rating, 48 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Nov 2 – 9

R2,865 ZAR per night

Guest favorite

Cottage in Deep River

4.89 out of 5 average rating, 19 reviews

Country Cottage in Private Garden Setting

Oct 24 – 31

R3,887 ZAR per night

Guest favorite

Cottage in Deep River

5.0 out of 5 average rating, 8 reviews

Serene Waterfront Cottage

Nov 22 – 29

R8,735 ZAR 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
R2,091 ZAR 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

Cabin in East Haddam

Home in Old Lyme

Home in Old Lyme

Apartment in Middletown

Guest suite in Wallingford

Tiny home in Guilford

Home in Essex

Loft in Westbrook

Other great vacation rentals in Essex

Guesthouse in Essex

Home in Haddam

Guest suite in Old Saybrook

Home in Essex

Apartment in Clinton

Home in Old Saybrook

Cottage in Deep River

Cottage in Deep River

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