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Essex Holiday Rentals

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Our top choices for Essex holiday 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, (201 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is NZ$359
includes taxes & fees
9 Nov - 10 Nov
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 NZ$321
includes taxes & fees
18 Oct - 19 Oct
1-bedroom cottage with Grove Beach 🏖️ access.

3. 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 NZ$432
includes taxes & fees
4 Nov - 5 Nov
Walk To Goodspeed Opera House!

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 NZ$616
includes taxes & fees
3 Nov - 4 Nov
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

5. 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, (15 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is NZ$787
includes taxes & fees
12 Oct - 13 Oct
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

6. 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 NZ$836
includes taxes & fees
15 Oct - 16 Oct
Adorable Cottage, 5 min walk to water & town

7. 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 NZ$508
includes taxes & fees
12 Oct - 13 Oct
The Stern at Soundview · Beach+Ocean+Sunrise

8. 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 NZ$969
includes taxes & fees
4 Nov - 5 Nov
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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, (62 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 NZ$475
includes taxes & fees
19 Oct - 20 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!

10. 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)
"Very clean and comfortable"
United States
Francine F.
Adorable Cottage with Cottage porch, walk to water & town

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, (29 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is NZ$522
includes taxes & fees
20 Oct - 21 Oct
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, (11 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is NZ$459
includes taxes & fees
3 Nov - 4 Nov
Lakefront Boho Tiny House

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 NZ$507
includes taxes & fees
4 Nov - 5 Nov
Cozy Lakefront Tiny House

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, (8 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 NZ$751
includes taxes & fees
11 Oct - 12 Oct
The Bay Cottage · Rocky Neck Park, Beach & Niantic

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$1,121
includes taxes & fees
3 Nov - 4 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green

16. 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 NZ$508
includes taxes & fees
12 Oct - 13 Oct
Freeboard at Soundview · Beach+Ocean+Sunrise

17. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Great spot Very clean"
United States
Dorothy W.
The price is NZ$866
includes taxes & fees
3 Nov - 4 Nov
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

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 Mast at Soundview · Beach+Ocean+Sunrise

19. 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 NZ$248
includes taxes & fees
14 Oct - 15 Oct
The Tiny Cottage & Mini Farm

20. The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.8 out of 10, Excellent, (3 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is NZ$463
includes taxes & fees
12 Oct - 13 Oct
The Anchor at Soundview · Beach+Ocean+Sunrise
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Essex holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Essex. 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 Essex. 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 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 holiday 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 Essex short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Essex?

Yes, there are holiday rentals in Essex close to Essex Steam Train, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Essex has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Essex is located on the beach, and has a balcony, a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Essex?

With 3 Expedia holiday rentals, you're guaranteed 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 holiday rental in Essex like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Essex. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.