A quaint white building with a dark shingled roof, a flag, and a sign reading "Toys Ahoy".

Essex Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Essex vacation rentals

A cabin with a dining table set for two, a bicycle, and a small porch area.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (195 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is AED 529
AED 777 total
includes taxes & fees
29 Oct - 30 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 440
AED 839 total
includes taxes & fees
26 Oct - 27 Oct
1-bedroom cottage with Grove Beach 🏖️ access.
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

3. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Old Saybrook
10.0 out of 10, Exceptional, (14 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is AED 735
AED 1,644 total
includes taxes & fees
4 Oct - 5 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
A beach with waves, a clear sky, and a sandy shore.

4. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is AED 805
AED 1,577 total
includes taxes & fees
11 Oct - 12 Oct
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A rocky shoreline with a beach and ocean in the background.

5. Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.2 out of 10, Wonderful, (9 reviews)
"Great location and a nice room!"
United States
Angela M.
The price is AED 507
AED 1,004 total
includes taxes & fees
1 Oct - 2 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise
A large, white, multi-story building with a prominent tower and a flag on top.

6. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveler
The price is AED 525
AED 907 total
includes taxes & fees
27 Oct - 28 Oct
Walk To Goodspeed Opera House!
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

7. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is AED 380
AED 511 total
includes taxes & fees
6 Oct - 7 Oct
The Tiny Cottage & Mini Farm
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

8. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is AED 608
AED 1,732 total
includes taxes & fees
1 Oct - 2 Oct
Adorable Cottage, 5 min walk to water & town
A stone pier leading to a beach with houses in the background.

9. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (61 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is AED 433
AED 1,019 total
includes taxes & fees
8 Oct - 9 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

10. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is AED 579
AED 1,092 total
includes taxes & fees
7 Oct - 8 Oct
The gardners Cottage 1 mile from long Island Sound - pet friendly
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

11. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (10 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is AED 513
AED 1,060 total
includes taxes & fees
20 Oct - 21 Oct
Lakefront Boho Tiny House
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

12. Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
9.0 out of 10, Wonderful, (8 reviews)
"Great host and property"
United States
Kevin K.
The price is AED 760
AED 1,925 total
includes taxes & fees
1 Oct - 2 Oct
Adorable Cottage with Cottage porch, walk to water & town
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

13. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is AED 505
AED 1,051 total
includes taxes & fees
1 Oct - 2 Oct
Cozy Lakefront Tiny House
A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

14. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (7 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is AED 492
AED 1,419 total
includes taxes & fees
1 Oct - 2 Oct
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

15. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is AED 1,058
AED 2,067 total
includes taxes & fees
12 Oct - 13 Oct
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A rocky shoreline with a beach and ocean in the background.

16. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (5 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
United States
Janine
The price is AED 507
AED 1,004 total
includes taxes & fees
1 Oct - 2 Oct
The Stern at Soundview · Beach+Ocean+Sunrise
A rocky shoreline with a beach and ocean in the background.

17. The Mast at Soundview · Beach+Ocean+Sunrise

The Mast at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This is a good option if you're looking for somewhere spotlessly clean and convenient to lay your head at night while you hit the beach during the day. The beach is steps away and lovely."
United States
Alison H.
The price is AED 507
AED 1,004 total
includes taxes & fees
1 Oct - 2 Oct
The Mast at Soundview · Beach+Ocean+Sunrise
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

18. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (37 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is AED 459
AED 948 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A beach with a house in the background, a clear sky, and a calm sea.

19. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is AED 555
AED 1,299 total
includes taxes & fees
4 Oct - 5 Oct
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Essex Hotel Reviews

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

8/10 Good
"The room was pleasant. The breakfast could have more options.."
Timothy 2-night trip
Posted 14 hours ago
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Frequently asked questions

Are there vacation rentals in Essex?

Yes, there are vacation rentals in Essex close to Essex Steam Train, or you can go with a more remote option if you're looking for a relaxing stay. Our travelers say Essex has a good selection of bars. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best vacation home rentals in Essex?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental near Essex is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Essex?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Essex stay.

What’s there to see and do in Essex?

Family-friendly attractions include Essex Steam Train and Sweet Martha's, whereas Connecticut River is a spot to enjoy the outdoors. Essex Island Marina and Essex Library are other places to visit while you're in town.

What’s a vacation rental in Essex like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Essex. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for families.