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Essex Vacation Rentals

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Our top choices for Essex vacation rentals

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, (194 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is CA $191
CA $285 total
includes taxes & fees
Oct 5 - Oct 6
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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 CA $169
CA $322 total
includes taxes & fees
Oct 26 - Oct 27
1-bedroom cottage with Grove Beach 🏖️ access.

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, (13 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is CA $324
CA $693 total
includes taxes & fees
Oct 1 - Oct 2
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

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 CA $144
CA $405 total
includes taxes & fees
Sep 29 - Sep 30
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

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 CA $184
CA $375 total
includes taxes & fees
Sep 29 - Sep 30
Freeboard at Soundview · Beach+Ocean+Sunrise

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 traveller
The price is CA $195
CA $340 total
includes taxes & fees
Oct 21 - Oct 22
Walk To Goodspeed Opera House!

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 CA $148
CA $198 total
includes taxes & fees
Sep 29 - Sep 30
The Tiny Cottage & Mini Farm

8. Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
The price is CA $202
CA $398 total
includes taxes & fees
Sep 29 - Sep 30
Keel at Soundview · Beach+OceanView+Sunrise

9. 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 CA $250
CA $691 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town

10. 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 CA $159
CA $388 total
includes taxes & fees
Sep 30 - Oct 1
Insta-worthy Couples Retreat: Perfect for romantic getaway!

11. 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 CA $223
CA $422 total
includes taxes & fees
Oct 7 - Oct 8
The gardners Cottage 1 mile from long Island Sound - pet friendly

12. 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 CA $191
CA $400 total
includes taxes & fees
Oct 20 - Oct 21
Lakefront Boho Tiny House

13. 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 CA $293
CA $746 total
includes taxes & fees
Sep 30 - Oct 1
Adorable Cottage with Cottage porch, walk to water & town

14. 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 CA $218
CA $431 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Lakefront Tiny House

15. 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 CA $169
CA $520 total
includes taxes & fees
Sep 30 - Oct 1
The Bay Cottage · Rocky Neck Park, Beach & Niantic

16. 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 CA $407
CA $801 total
includes taxes & fees
Sep 30 - Oct 1
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

17. 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 CA $184
CA $375 total
includes taxes & fees
Sep 29 - Sep 30
The Stern at Soundview · Beach+Ocean+Sunrise

18. 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 CA $184
CA $375 total
includes taxes & fees
Sep 29 - Sep 30
The Mast at Soundview · Beach+Ocean+Sunrise

19. 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 CA $177
CA $362 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

20. 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 CA $206
CA $491 total
includes taxes & fees
Oct 6 - Oct 7
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.
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Top Essex Hotel Reviews

Find out more about Essex

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Essex. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.