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House vacation rentals in Essex

Find and book unique houses on Airbnb

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Popular amenities for Essex house rentals

House rentals with a pool

Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars7 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favorite
A light-filled living area features a neutral-colored sofa alongside a blue couch, with decorative pillows adding subtle color. A wooden coffee table rests in front, and large windows with bamboo shades allow natural light to brighten the space.
Home in North Fork
4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

EricRating, 5 stars7 months ago
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.
Guest favorite
A light-filled dining area features a round wooden table surrounded by four white chairs. French doors open to a lush outdoor space, and the wood-beamed ceiling adds a rustic touch. The adjacent kitchen with white cabinetry is partially visible, enhancing the open feel.
Home in East Hampton
4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars3 weeks ago
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.
Superhost
A modern home is showcased with a unique angular design, featuring a combination of wood and glass. The surrounding lawn is spacious and well-maintained, with natural landscaping, including grasses and a small tree, contributing to the serene outdoor setting.
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars7 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars4 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Top guest favorite
The outdoor area features a large in-ground pool surrounded by a fence, with lounge chairs and shaded umbrellas. A spacious wooden deck is visible, along with seating and a small shed. The lush greenery of the backyard complements the serene setting.
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favorite
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Top guest favorite
A welcoming living area showcases a light grey sofa and two upholstered chairs flanking a coffee table. Natural light floods the space through large windows, highlighting a collection of framed artwork on the wall. A modern chandelier adds a stylish touch overhead.
Home in East Hampton
5 out of 5 average rating, 36 reviews

Stunning Central E. Hampton Home w/ gunite pool.

DonnaRating, 5 stars3 months ago
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!

Weekly house rentals

Guest favorite
A two-tiered wooden display stands on a dining table, showcasing starfish and decorative stones. The lower section features a painted image of a manatee against a green background, while the upper level displays additional starfish. Natural light illuminates the table's wooden surface.
Home in Westerly
4.94 out of 5 average rating, 18 reviews

Beach House Minutes to relaxing by the ocean

CeciliaRating, 5 stars7 months ago
I don’t say this often but the house was even more perfect in person. So cute with great amenities. The hosts were amazing. The area has so much to do and all so close ! Can’t say enough good things!
Superhost
The open living area features vaulted ceilings with exposed wooden beams. A cozy seating arrangement includes a sofa and accent chairs around a circular coffee table on a textured rug. Natural light enters through large windows dressed with curtains, enhancing the spacious environment.
Home in Charlestown
4.83 out of 5 average rating, 29 reviews

Quonnie Beach House Walk to the beach

JohnRating, 5 stars2 months ago
My main search was for a pet friendly rental so I could invite friends with a senior golden retriever. And secondly I wanted to be near the ocean. Having lived on Cape Cod for 25 years, I moved back to Connecticut a year ago after the passing of my wife. But the call of the ocean never fades and this rental was steps from East Beach. My stay was in February and the weather wasn't the best, but beach walks are always best when the only footsteps in the sand are your own. The rental was very accommodating with 3 bedrooms, a spacious living area and large, fully equipped kitchen. Plenty of outdoor seating is also included. Melissa was very attentive and always responded quickly when needed. I definitely recommend this rental for a peaceful adult retreat or for a full family vacation. Kids will love it with the big yard and kayaks available. Enjoy, John
Guest favorite
A black lounge chair is positioned beside large glass doors, offering views of Napeague Harbor. Natural light fills the space, highlighting the warm wooden floors and nearby outdoor seating. A shading sail is visible outside, along with a pop of red from an umbrella.
Home in Amagansett
4.93 out of 5 average rating, 14 reviews

Amagansett, Waterfront retreat

DanielleRating, 5 stars7 months ago
My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!
Guest favorite
Home in North Fork
4.97 out of 5 average rating, 254 reviews

The Greenport Bungalow

SaraRating, 5 stars3 weeks ago
This is an AMAZING Airbnb. High quality blankets, towels, ornamental details throughout the space. Comfortable beds. Beautiful ambient lighting. Large backyard with a fire pit. The neighborhood is quiet, beautiful houses, surrounded by water, with lovey little shores and nooks to walk to. My 4 year old had toys to play with and a little potty that all came with the home. I will DEFINITELY stay again. My family and I loved this place.
Top guest favorite
A blue bungalow exterior is shown, featuring a spacious deck with black railings and multiple glass doors. A picnic table is situated on the lawn, alongside a children's toy. Lush greenery surrounds the property, enhancing the setting.
Home in Montauk
5 out of 5 average rating, 20 reviews

Montauk beach house!

StephanieRating, 5 stars6 months ago
Lovely, well kept and comfortably furnished. This home has everything you need for a comfortable stay. Owner is helpful and very responsive. Highly recommened!
Guest favorite
A bright, open-concept living area features a large wooden dining table surrounded by textured chairs. Expansive windows invite natural light and showcase views of the surrounding greenery. A cozy seating area is arranged near a fireplace, with modern decor enhancing the space's aesthetic.
Home in Montauk
4.95 out of 5 average rating, 38 reviews

Lux Montauk Retreat:Pool,Water Views,Sunsets Deck

KathleenRating, 5 stars7 months ago
I cannot say enough amazing things about this house - our stay was absolutely sublime. The decor was immaculately curated, the house had all the supplies required to cook family meals, the sunset was to die for, and we had an absolute blast at the pool. Communicating with Dan and Tabitha was great, very professional and responsive. The home was incredibly clean - it was the nicest AirBnb I've ever stayed in BY FAR, already looking forward to booking again. THANK YOU!
Guest favorite
The front exterior of the home is framed by lush greenery and a flower-lined pathway made of stone. Two trees add natural shade, while a charming yellow door welcomes guests. A fenced yard and gravel accents enhance the inviting entrance.
Home in North Fork
4.94 out of 5 average rating, 108 reviews

Maritime Village Getaway with Backyard

NicoleRating, 5 stars3 months ago
We had such a wonderful stay here over New Years. Like many other reviews have stated, pictures do not do this home justice. It’s so much larger and more spread out than we expected. Perfect layout for two couples where we each felt like we had our own place, with plenty of cozy spaces to hang out too. The kitchen is SO well equipped for anything and everything. Beds and sofas were super comfortable and the we loved all of the charming touches of this historical home. The location is fantastic too. Walking distance to everything you could need and a quick drive to so many beautiful areas. I can imagine spending hours in the backyard when the weather is warmer too!
Guest favorite
A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.
Home in East Lyme
4.96 out of 5 average rating, 186 reviews

Beachfront Paradise

DavidRating, 5 stars1 month ago
We stay at Patti's place twice a year for a time of reflection. The location is peaceful and restful, right on the water. Patti always has a plate of cookies waiting for us and lets us know about any changes. We had a cold, wet first day, so were particularly delighted to be able to use the new gas fireplace, which kept everything warm and cozy. We're booked in for late fall already!

Private house rentals

Guest favorite
The exterior of a single-story home is set among lush greenery, featuring a varied facade with shingle and clapboard elements. Symmetrical landscaping includes neatly trimmed shrubs and a spacious lawn. A pathway leads to the front door, framed by tall trees providing natural shade.
Home in Shelter Island
4.88 out of 5 average rating, 26 reviews

Peaceful and Private 3 bedroom home in the woods

Robert,Donald JrRating, 5 stars8 months ago
Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!
Superhost
The exterior view of the house is shown, featuring a clean white facade and large glass doors. A spacious deck is visible on the second floor. A wooden bench is positioned on a stone patio, surrounded by well-maintained greenery.
Home in Stonington
5 out of 5 average rating, 3 reviews

Shell House

MariaRating, 5 stars8 months ago
The home was exactly as described! It was lovely. A serene and peaceful vibe throughout and in the yard. both roomy and spacious. We were even surprised to get a water view from the top deck! All and all the house was very well appointed with everything we needed from chef quality pots and pans and dishes as well as a new out side gas grille! Beautiful artwork through out! Julie was great to work with and gave us excellent ideas for what to do and where to go in the area. We will surely go back! A great place for couples or a family with children.
Guest favorite
The exterior of a two-story single-family home is depicted, featuring beige siding and a centered front door. Lush green grass surrounds the walkway leading to the entrance, with a mailbox positioned at the pathway. A nearby tree and hedges provide additional greenery.
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago
It was wonderful stay and I’d go back anytime
Superhost
A two-story home features a welcoming front porch with steps leading up to it. A gravel driveway is visible, bordered by lush greenery and flowering bushes. Bicycles can be seen propped against the house, surrounded by a peaceful, natural setting.
Home in East Hampton
4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

AntoineRating, 5 stars7 months ago
Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back
Top guest favorite
The exterior of a charming two-story house is presented, featuring light siding and dark shutters. Window boxes adorned with blue flowers are visible. A small porch with a door leads into the home, accompanied by a stone pathway and neatly landscaped shrubs.
Home in Old Saybrook
4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

SueRating, 5 stars6 days ago
Laurie s place is very nice, spacious and clean. Plenty of space to eat, hang out and 2 bath. The fenced in yard is great for dogs or kids. We weren't in full summer season so we're not taking advantage of the beach and water options but they offer alot. Allowed for an early check in which was great as we were in town for a memorial service.
Guest favorite
The white estate is framed by bare trees, showcasing a combination of traditional architecture and natural surroundings. A serene lawn is visible in the foreground, with stone walls adding rustic charm. Soft lighting illuminates the porch, creating a welcoming atmosphere.
Home in East Haddam
5 out of 5 average rating, 25 reviews

Elegant Countryside Estate

AnjaliRating, 5 stars4 months ago
Spent a wonderful Thanksgiving weekend at Travis' place with my husband and two young daughters. The house is beautifully appointed and so cozy. We played games by the fire, watched a movie in the cozy tv room, and made and enjoyed lovely meals in the kitchen. The house is even more magical than it looks in the photos, and we certainly hope to be back.
Guest favorite
A wooden walkway leads down to a calm beach, with gentle waves lapping at the shore. The water reflects a clear sky and distant land. A floating object is seen in the water, enhancing the serene coastal scene.
Home in North Fork
4.92 out of 5 average rating, 12 reviews

Private Beach access along the Wine Trail

RaeganRating, 5 stars1 month ago
I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!
Guest favorite
A private country compound is showcased, featuring a main house with a classic white exterior and black shutters. A blossoming tree stands prominently in the foreground, surrounded by a well-maintained lawn and neatly trimmed hedges.
Home in Sag Harbor
4.85 out of 5 average rating, 262 reviews

Exclusive Sag Harbor Compound

WyattRating, 5 stars5 months ago
We loved our stay here. The house was sparkling clean and the yard was big and beautiful. Can only imagine the vibes here during the summertime when the pool is open!

Quick stats about house rentals in Essex

  • Total rentals

    20 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    910 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

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  4. Middlesex County
  5. Essex
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