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

Essex Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Essex vacation rentals

View from property

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, 187, (187 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is ￥20,760
￥30,940 total
includes taxes & fees
Sep 22 - Sep 23
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Exterior

2. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, 42, (42 reviews)
"Very convenient location with good parking"
United States
Anonymous traveler
The price is ￥24,578
￥41,245 total
includes taxes & fees
Oct 6 - Oct 7
Walk To Goodspeed Opera House!
Room

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, 56, (56 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥18,525
￥35,566 total
includes taxes & fees
Oct 6 - Oct 7
1-bedroom cottage with Grove Beach 🏖️ access.
Interior

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

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, 17, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥25,438
￥72,441 total
includes taxes & fees
Sep 15 - Sep 16
Adorable Cottage, 5 min walk to water & town
Room

5. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, 10, (10 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is ￥20,445
￥43,006 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront Boho Tiny House
Beach

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, 60, (60 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 ￥19,201
￥44,332 total
includes taxes & fees
Sep 29 - Sep 30
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Exterior

7. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, 5, (5 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is ￥22,473
￥45,645 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Lakefront Tiny House
Private kitchen

8. 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, 28, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is ￥26,882
￥47,696 total
includes taxes & fees
Oct 7 - Oct 8
The gardners Cottage 1 mile from long Island Sound - pet friendly
Dining

9. 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, 8, (8 reviews)
"Great host and property"
United States
Kevin K.
The price is ￥33,564
￥82,862 total
includes taxes & fees
Sep 15 - Sep 16
Adorable Cottage with Cottage porch, walk to water & town
Cottage (1 Bedroom) | Front of property

10. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
3.0 star property
Montville
10.0 out of 10, 3, (3 reviews)
"The pool was amazing, the host was great, very accessible and the property was prisine. The views alone made us immediately want to come back. Very clean and well stocked. "
United States
agata
The price is ￥25,346
￥58,321 total
includes taxes & fees
Sep 16 - Sep 17
Private Guest House w/ Deck + Spectacular Views!
Interior

11. 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, 140, (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 ￥44,240
￥86,437 total
includes taxes & fees
Sep 21 - Sep 22
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Beach

12. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, 2, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥25,008
￥82,561 total
includes taxes & fees
Sep 15 - Sep 16
Beachside Bliss w/ Game Room, Gym & Golf Green
Pool

13. Private Guest House w/ Deck + Spectacular Views!

Private Guest House w/ Deck + Spectacular Views!
Montville
10.0 out of 10, 41, (41 reviews)
"I had a pleasant stay, the house is very clean, well-equipped, and the peace and quiet were perfect. I commend the owner."
United States
Faniola O.
The price is ￥18,894
￥55,361 total
includes taxes & fees
Sep 16 - Sep 17
Private Guest House w/ Deck + Spectacular Views!
Living area

14. 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, 13, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ￥38,403
￥78,956 total
includes taxes & fees
Sep 20 - Sep 21
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Living area

15. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, 11, (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 ￥17,665
￥23,387 total
includes taxes & fees
Oct 6 - Oct 7
The Tiny Cottage & Mini Farm
Beach

16. 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, 1, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is ￥22,811
￥52,155 total
includes taxes & fees
Sep 28 - Sep 29
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Living area

17. 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, 36, (36 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 ￥20,584
￥41,375 total
includes taxes & fees
Sep 22 - Sep 23
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Dining

18. LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!

LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Clinton
9.8 out of 10, 6, (6 reviews)
"Was very happy with how wonderfully beautiful the place was. The host was excellent and answered any questions I had promptly. I really appreciate how nice he was."
United States
Elizabeth C.
The price is ￥45,315
￥116,244 total
includes taxes & fees
Sep 28 - Sep 29
LONG TERM-Fall is coming, Leaves Colors, Beach, Golf, Outlets!
Interior

19. Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, 33, (33 reviews)
"The home is very well kept and is in a wonderful location. We enjoyed it a great deal and would go back in a heart beat."
United States
Chrissy R.
The price is ￥32,258
￥61,674 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Marina

20. Clean room w/ King bed/Private bathroom. Free Wifi free parking

Clean room w/ King bed/Private bathroom. Free Wifi free parking
New London
9.8 out of 10, 19, (19 reviews)
"Stayed for two nights. Such a great location to the coast guard academy and lots of little restaurants and places to visit. Bill is a great host and very eager to provide a comfortable stay. "
United States
Julio J.
The price is ￥16,590
￥22,151 total
includes taxes & fees
Sep 15 - Sep 16
Clean room w/ King bed/Private bathroom. Free Wifi free parking
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.
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Top Essex Hotel Reviews

North Fork Resort

North Fork Resort

10/10 Excellent
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
Harold 1-night trip
Posted less than an hour ago
North Fork Resort

Find out more about Essex

Search for holiday rentals in Essex on Expedia! You can easily find your home rentals, villas, holiday apartments in Essex using one of the methods below:

  • View our selection of featured holiday rentals in Essex
  • Use the map to find apartments and other holiday homes in the Essex neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Essex while they last

Look no further and take a look at our great range of rental properties in Essex!

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 Pratt House 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.