12 Best Airbnb Vacation Rentals In Essex, Connecticut - Updated 2024

airbnb Essex CT
Lilian
Lilian 
Updated
| 5 min read

If you haven’t been to Essex, Connecticut, you haven’t been anywhere! Not only does it feature in the New York Times Bestseller as one of the 1,000 Places To See Before You Die, but it is also considered one of the best small towns in the United States. Featuring an eclectic mix of history and art, this coastal town offers visitors much to explore and plenty of things to do. Visit the historic museums and art galleries during the day, or soak in awe of the Colonial and Federation-era architecture along the streets. Enjoy a riverboat ride along the Connecticut River during sunset and take in the spectacular view of this harbor town.

There are also plenty of cafes, shops, and restaurants to visit throughout the day. You can also go on a day trip and try some of the best things to do in New London less than 30 minutes away! Complete your vacation with high-quality rest. Keep reading to learn about the best Airbnb vacation rentals in Essex, Connecticut!

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 02, 2024.

1. Cozy home with a fireplace (from USD 285)

This pet-friendly Airbnb in Essex, Connecticut, offers a cosy abode for your Essex vacation! It is ideally located near Sunset Pond, Falls River, and is within walking distance of downtown where you can find many shops and food establishments. At night, stay warm and toasty by the living room fireplace while you watch a movie on the flat-screen TV or read a book on the plush sofa. In the mornings, you can enjoy your coffee in the sunroom to enjoy the view or, if it’s not too cold out, sit on the private patio to breathe fresh air.

Stayed at this property?
Essex, Connecticut, United States
7.94 km (5.0 mi) from Gillette Castle State Park
30 reviews   Superhost Wifi Available
Entire cottage 2 Beds 4 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
nice ceiling fan in the master and good ac
great kitchen-backyard lights and water feature-indoor porch too
and the generous access to streaming services comfortable and elegant bedding and shower bath and amenities
enclosed porch overlooking garden would be lovely extra room in warm weather
the beds were comfortable with beautiful linens and the kitchen was updated and well equipped
Cleanliness:
everything you could need is there but the space still manages to feel wonderfully clean & uncluttered
nice cottage with comfortable beds very clean and close to historic area
Host:
wes and jody were great hosts
the owners were very responsive and easy to communicate with
had a few interactions with the hosts as well & they were lovely & responsive
wesley is very responsive and helpful
wesley and jody were terrific hosts: incredibly responsive and caring
Location:
great location walk to beautiful riverside streets downtown shops & restaurants also near public tennis courts / playground
the bonus was the location just a short walk to town
good access to the town and we enjoyed walking
this was a lovely home very close to the heart of essex
the location is great and was very convenient for my husband dog and i
Read more reviews

2. Charming guesthouse with a garden view (from USD 220)

Enjoy beautiful views of the garden while you sit on the private patio on this holiday rental in Essex, Connecticut. If you come during the right season, you might even see the charming wisteria vines climbing up the pergola to provide shade. On lazy afternoons, head down the river and sit on the riverside chairs or if you’re feeling adventurous, dip your toes in the water! You can also wait for the late afternoon and enjoy roasting marshmallows while huddled around the fire pit.

Stayed at this property?
Essex, Connecticut, United States
7.21 km (4.5 mi) from Gillette Castle State Park
25 reviews   Superhost Wifi Available
Entire guesthouse 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
tech/internet was super with fast internet speeds and great wifi coverage
the beds were the most comfortable i've experienced in an airbnb
it is cozy and comfortable and had everything we needed
Cleanliness:
inside is clean comfortable and well stocked
the guest house is clean and very well appointed
the beds were clean and comfortable and the bathroom was well stocked
the beds and linens are very comfy and everything was super clean and comfortable
it’s also super clean with lovely linens and comfortable beds
Host:
reninca is a great host
she was very responsive and quick to help when needed
hosts are marvelous and essex is full of charm
reninca was so kind to meet my mom beforehand to tour the house
the hosts are helpful and responsive and very pleasant to deal with
Location:
downtown was just a short walk away and the neighborhood is a joy to walk through
it is the perfect location if you are visiting the area for the first time
we especially enjoyed hiking at gillette castle state park on thanksgiving day
it's a great place to stay
what a treasure we found reninca's guesthouse a perfect place to stay whole visiting friends in essex
Read more reviews

3. Open-concept studio apartment near Connecticut River (from USD 114)

Pamper yourselves with a stay at the Cozy Nook! This spacious, open-concept studio apartment rental in Essex, Connecticut, promises a home away from home. It is located in a peaceful country neighborhood and makes an ideal choice for a getaway. Nature lovers will love the endless hiking trails, beaches, and close proximity to the Connecticut River. Also, it is conveniently located near dining spots that will whet your appetite, theatres, and galleries that will keep you entertained and shopping.

Enjoy the best of both worlds by staying between New York and Boston – who says you can’t have both? The Cozy Nook guarantees a stay of absolute comfort!

Stayed at this property?
Essex, Connecticut, United States
9.92 km (6.2 mi) from Gillette Castle State Park
124 reviews   Wifi Available
ENTIRE HOME 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
we also had fresh blueberry muffins coffee and champagne in our little kitchen when we got there
doree's cozy nook is a lovely apartment with all the amenities plus that one could possibly need
doree's place was perfect for our needs -- cozy beds and definitely a cozy nook for our stay
at night the temps went down and the basement level suite was still quite comfortable for sleeping
our stay at the cozy nook was perfect
Cleanliness:
very clean and well kept
the apartment was spotless and it was clean
spotless with lovely decor
doree’s place is clean and comfortable
pretty clean and comfortable
Host:
great host: helpful but unobtrusive
doree is a wonderful host and is easily accessible
doree is a very caring and helpful host
she and her husband we very warm and kind
doree was a kind and gracious host who even provided some refreshments upon our arrival
Location:
gem beautiful location nestled in the woods
awesome location and a beautiful place to stay loved the decor
i spent a week here and found the location very peaceful
the place was also really cute and homey
the house is located in a calm neighborhood surrounded by a large garden and huge trees
Read more reviews

4. Quaint retreat with views of Connecticut River (from USD 105)

Across the street from the Connecticut River, this quaint 1800s vacation house for rent in Essex, Connecticut makes for a relaxing, enjoyable vacation. It is an ideal location to explore New England towns and watch the iconic Essex Steam Train or the picturesque Becky Thatcher Riverboat. There are a plethora of activities down at the Connecticut River to participate in, or you can enjoy a cocktail while people-watching on the balcony, overlooking the river. Enjoy the absolute comfort of this home designed to make you feel at home.

Stayed at this property?
Deep River, Connecticut, United States
3.07 km (2.0 mi) from Gillette Castle State Park
220 reviews   Superhost Wifi Available
Entire cottage 2 Beds 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
beautiful post card view from the bed
wifi was a bit spotty but best to unplug anyway
quite charming and comfortable and the cottage was much larger than i anticipated
plenty of space and nice to have a kitchen too
adorable cottage perfect spot and comfortable for 2 people
Cleanliness:
the cottage is clean and adorable
the cottage is adorable and super clean and comfy
convenient and very clean
this cottage was cozy clean and lovely
quaint and clean spacious cottage close to the water
Host:
andrea is a very good host
wonderful host adorable small town
andrea is a very friendly and helpful host
andrea is a very helpful person
andrea was also very kind and quick to communicate
Location:
great location near the river
great location and charming character
cute cottage in a wonderful location
nice place in a great location
a good value excellent location
Read more reviews

5. Cosy apartment with river views (from USD 115)

This is an ideal location for train aficionados, as you can watch and capture the famous Essex Steam Train in action. Enjoy a vacation in this comfortable and private apartment with a spectacular, close up view of the Connecticut River and one that overlooks the iconic Becky Thatcher Riverboat.

Interestingly, this vacation rental in Essex used to be part of a historic building, built in 1874. It is, however, nicely furnished with heat controls and a modern kitchen. This building welcomes wedding events, as well!

Stayed at this property?
Deep River, Connecticut, United States
3.2 km (2.0 mi) from Gillette Castle State Park
169 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
river views and comfortable
we enjoyed the quiet space and the views from the room
wonderful cozy place with great water views and access across the street
it was a very cosy apartment with a great view of the ct river
what an unexpectedly large and beautiful apartment the view is terrific and the grounds are lovely too
Cleanliness:
very clean place with a comfortable bed
cozy warm clean and super cute
the apartment was clean and we had nearly everything we needed (as per listing)
(it doesn't run at night so don't worry about train noise ) the apartment was clean and comfortable
the view is wonderful the apartment was clean and well kept
Host:
andrea was a lovely host
andrea and company are professional and gracious hosts
lovely home lovely setting and lovely host
andrea was very helpful accommodating and communicative
private nice apartment and friendly host
Location:
cute place in a great location
perfect location for our ct river excursion eagle/osprey trip
good location- short walk to river
the location is spot on for a great little get away at any season
lovely location private and quiet
Read more reviews

6. The Nest (from USD 121)

Nestled in a peaceful country neighbourhood with endless hiking trails, beaches, and cosy villages nearby, the Nest is an absolute gem that guarantees comfort and convenience in a beautiful environment. This unique Airbnb in Connecticut sports bright and cheery decor and invites guests on a getaway vacation, any time of the year.

Located between Boston and New York, guests may experience the best of the two cities at this vacation rental. Also, this clean and spacious apartment offers modern living with brand new amenities, a fully-furnished kitchen with island seating, a huge bathroom, as well as a large, stone firepit. It is an absolute must-visit in your lifetime!

Stayed at this property?
Essex, Connecticut, United States
10.12 km (6.3 mi) from Gillette Castle State Park
94 reviews   Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
nicely appointed place with extra touches such as coffee and breakfast each morning
the bed was extremely comfortable
we had wonderful cozy nights and a good nights sleep
Cleanliness:
great place clean and well stocked
super clean nicely decorated and furnished
the space was immaculately clean impeccably well stocked and beautifully decorated
the nest is sparkling clean and so comfortable
the nest was clean cozy and comfortable
Host:
doree was a wonderful host
doree is a great host
doree is a great host
thank you doree for being a super host
doree was a fantastic host
Location:
the location was quiet and peaceful
it was close to great restaurants and beautiful walks
perfect location relaxing and many places to explore
everything was so close as well
convenient location and wonderful amenities
Read more reviews

7. Historic mansion in Old Lyme (from USD 171)

Travel back in time - yes, you can! This picturesque vacation rental offers an apartment on the third storey of the historic Old Lyme Mansion, in the charming village of Old Lyme. It overlooks beautiful grounds and a historic church, just next door! Not only does the exterior look stunning, the interior sports modern, yet stylish décor.

It is also within close proximity to restaurants, beaches, art galleries and museums. This is a perfect choice for families or travellers in search of a private, relaxing vacation.

Stayed at this property?
Old Lyme, Connecticut, United States
14.67 km (9.2 mi) from Gillette Castle State Park
180 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 5 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
window air conditioners kept us comfortable despite "excessive heat warning" days outside
we enjoyed the beautiful rooms the country views and the quietness
the beds and linens were super comfy
this apartment was so cute very clean with all of the amenities you could need
holly's place was so comfortable and had everything we needed at hand
Cleanliness:
sparkling clean accommodations were greatly appreciated
clean safe and absolutely adorable
plenty of room & was very clean
the rooms were roomy and very clean
3rd floor was very nice and clean
Host:
the hosts were friendly and eager to make our stay comfortable
holly and berry were delightful hosts
the hosts were great and easy to communicate with
holly was very accommodating and a great host
the home made ginger cake was a very kind welcoming touch
Location:
location was great and close to nice restaurants
wonderful spot in a wonderful location
the location is central to the other charming coastal villages in this area of connecticut
this is a beautiful home in a location convenient to many points of interest and activities
area is scenic and close to many attractions and restaurants
Read more reviews

8. Pet-friendly apartment best for families (from USD 158)

Have a unique vacation in Essex, by staying at the home of the former Erickson-Davis Gallery. This charming yet modern apartment is located in a quiet residential neighbourhood, just off Main Street. Not only is this Airbnb in Essex, CT, good for entertaining guests, it also has a large office area available, for guests to do their work. This spacious loft is an ideal choice for a getaway close to nature, as well as conveniently located to restaurants and amenities.

Stayed at this property?
Essex, Connecticut, United States
8.48 km (5.3 mi) from Gillette Castle State Park
400 reviews   Superhost Wifi Available
Entire loft 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
beds were super comfortable and the "extras" such as coffee cream etc
the beds were super comfy
well appointed kitchen complete with yummy cupcakes
i loved the openness of floor plan and the uniqueness each space of the apt/loft
beds were very comfy lovely linens hot water and a divine soaking tub
Cleanliness:
it was clean and artistic place
very eclectic very clean and comfortable
the atmosphere was comfortable while still being very clean and unique
was very clean and had so many interesting and amazing features
we cooked dinner and breakfasts and found the kitchen to be clean and just right
Host:
pam was a wonderful host
pam was a great host
host is responsive and thoughtful
pam is a gracious host and i look forward to visiting again
pam was extremely kind and helpful
Location:
quite location with easy access to downtown essex
good value and great location
beautiful place great location
what a lovely place to stay in a beautiful location
great location easy to get around and plenty of parking if you need it
Read more reviews

9. Old two-bedroom, one-bath loft in Saybrook

Experience Old Saybrook at this cosy and quiet loft, located on the third floor of a colonial building. This accommodation offers a private bedroom, a spacious living room with cable television and its own ensuite marble bathroom.

It is conveniently located near the highways that give easy access to many of the key attractions in Essex – only minutes away from the iconic Essex Steam Train, the Connecticut River Museum, Lyme Art Academy, Griswold Museum, Norma Terris Theater and much more! Guests also get a free beach pass to the Saybrook Town Beach during the summer and the Turtle Creek Wildlife Sanctuary is just within reach.

Stayed at this property?
Old Saybrook, Connecticut, United States
12.12 km (7.6 mi) from Gillette Castle State Park
87 reviews   Wifi Available
PRIVATE ROOM IN HOME 3 Beds 5 Guests 1 Bedroom 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
the rooms and bathroom were beautifully renovated and even better than expected from the photos
we felt comfortable immediately and enjoyed having our own space in the loft
there is a lovely living room with cable tv where you can spend time relaxing
it felt like a mini hotel room on her top floor
the space was incredibly clean with a large bathroom and multiple sleeping options
Cleanliness:
everything is clean and the beds are comfortable
the room was clean and spacious
very hospitable and extremely clean place
the house is very clean and quiet
the space is clean and comfortable and the bathroom is beautiful
Host:
we enjoyed this lovely home and the great hosts
the owners are so welcoming
the hosts are quite gracious
they are wonderful hosts who make you feel very much at home
hosts were gracious and helpful
Location:
the general location is beautiful
nice accommodations in a great location
ideal location for us- right off the highway
quiet picturesque location near the shore
the property is very close to two amazing restaurants and the water
Read more reviews

10. Refurbished farmhouse with pool and hot tub

Experience the best of coastal Connecticut with a stay at this bucolic farm. You will enjoy a relaxing vacation and wake up to the stunning landscape of hills and a scenic river during your stay. Built in 1737, this farmhouse can house up to 12 guests in their seven charming bedrooms. This place is ideal for a family vacation, engagement parties, or large gatherings.

It is completely furnished with complete amenities and even more - a large kitchen, a pool with pool house, a hot tub, woodburning stove and a lovely garden. Nature lovers will definitely enjoy basking in the forest gazebo or taking a walk to the barn, to watch the caretakers feed the horses.

Stayed at this property?
Lyme, Connecticut, United States
7.82 km (4.9 mi) from Gillette Castle State Park
100 reviews  
Entire house 8 Beds 7 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
the grill is fantastic as is the kitchen
the house was a magical wonderland filled with thoughtfully placed treasures and cozy places to spend quality time
the pool where we enjoyed the water and views
the house is beautifully restored with an amazing view great pool and also very soothing atmosphere
the pool is so nice it almost seems like an infinity pool with the view
Cleanliness:
had a great stay clean with plenty of space and a very unique house with all of the art
Host:
camomile was a nice and helpful host
she was so responsive and lovely
host was great but did take some time to answer our questions
camomile was really helpful and accommodating
the owner is quick to respond professional & made the stay very easy
Location:
the location is just amazing
walking distance to fox hopyard a great golf course
the perfect location for a long weekend away with the extended family i would highly recommend
it was the perfect trip at the perfect place
great location close to hiking beaches or golf
Read more reviews

11. Chalker Beach House

Beach lovers, look no further! There is no better place to stay than this luxurious beach house, located in the heart of Chalker Beach. You will enjoy the beach facilities, the clubhouse, onsite beach parking pass and plenty of shopping and dining.

This beautifully-furnished, three-bedroom beach house is perfect for getaways, retreats and celebration parties. Watch the sunrise (if you’re an early riser) or the sunset, with a cup of coffee or glass of wine in the open backyard. It is a beautiful choice, not to be missed.

Stayed at this property?
Old Saybrook, Connecticut, United States
15.6 km (9.7 mi) from Gillette Castle State Park
65 reviews  
Entire house 7 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
nice backyard with patio table and chairs for 8
wi-fi and tv work great
the kitchen does not have ac but sufficient fresh air cosmetics through the 2 windows
we had a hot week so a/c was a nice relief
the natural lighting in every room was also a huge plus
Cleanliness:
upon arrival the place was very clean and organized
the house was clean
house was clean and well taken care of
this house exceeded our expectations very spacious clean and comfortable
the house was well maintained clean and accurate to photos
Host:
deborah is a fantastic host
deborah was very responsive to questions that came up
deborah was a great host - she responded extremely quickly any time we had questions
deb was super responsive to any little questions we had
deborah was very responsive
Location:
great location private yet close to everything
great location close to beach but also centrally located to many other new england attractions
we loved how close to beach the house is
hope to visit during summer next time to enjoy the seaside location even more
this was the perfect location for my combined work and play trip to ct
Read more reviews

12. Old apartment in Saybrook

Come stay in a centralized location in Old Saybrook, near the Connecticut River at the best Airbnb in Essex. Not only is this place ideal for a relaxing vacation, it is also a cosy place for special occasions. Enjoy the best of Old Saybrook with its beaches, wildlife sanctuary, minigolf course, spa, museums, vineyard, shopping and dining - perfect to check-off the list of things to do in Essex.

This ensuite bedroom is located on the second floor of a new colonial house, with easy access to the highway and Amtrak train. Enjoy a comfortable quiet evening with a cup of tea or a glass of wine at the firepit in the backyard.

Stayed at this property?
Old Saybrook, Connecticut, United States
12.14 km (7.6 mi) from Gillette Castle State Park
170 reviews   Wifi Available
PRIVATE ROOM IN HOME 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the ac unit in the room was so nice
the room was private quaint and a/c was terrific with how hot it was outside
coffee and pastries for breakfast was a great bonus also
the room decor was both cheering and lovely
wonderful hospitality (fruit + coffee in the morning fresh flowers in our room)
Cleanliness:
and everything was very clean
the room is clean and very comfortable
everything was amazingly comfortable clean and quiet
immacuually clean great bath products and a beautiful area
the room is clean comfy and the bad is wonderful
Host:
an amazing home with amazing hosts
the hosts are friendly and helpful
sondra and victor were wonderful hosts
lovely warm hosts with tons of great recommendations
victor and sondra were great hosts
Location:
this is a good location for exploring the area
a beautiful house in a beautiful location
the location was perfect to accommodate us and very near the location for the wedding we were attending
very nice home great location and proximity to town
great place great location lovely bike rides through rural towns and the coastline
Read more reviews

Cosy in Connecticut

When nature and picturesque scenery call out to those seeking some respite, answer the call - slow down and enjoy the view. There’s no other place that will make you feel as cosy as these vacation rentals will, in Connecticut!

Stayed at this property?

Frequently asked questions about Airbnb vacation rentals in Essex, Connecticut


Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Lilian Tan is a creative storyteller, videographer and producer based in Singapore. She's an explorer at heart, and a writer by choice. She draws her influences from her observations on the beauty...Read more

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