A sandy beach with a breakwater, calm sea, and a clear sky.

Westbrook Vacation Rentals

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Our top choices for Westbrook vacation rentals

1. 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 $206
CA $487 total
includes taxes & fees
Oct 20 - Oct 21
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

2. 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 $223
CA $660 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town

3. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Getaway-Near Beaches, Train & Shoreline
Westbrook Center
The price is CA $283
CA $412 total
includes taxes & fees
Oct 19 - Oct 20
Westbrook Getaway-Near Beaches, Train & Shoreline

4. 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 CA $289
CA $844 total
includes taxes & fees
Oct 20 - Oct 21
Beachside Bliss w/ Game Room, Gym & Golf Green

5. 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 CA $289
CA $678 total
includes taxes & fees
Oct 20 - Oct 21
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

6. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (61 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $148
CA $301 total
includes taxes & fees
Oct 21 - Oct 22
1-bedroom cottage with Grove Beach 🏖️ access.

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
The price is CA $240
CA $432 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums

8. 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 CA $181
CA $273 total
includes taxes & fees
Nov 12 - Nov 13
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

9. 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 CA $224
CA $429 total
includes taxes & fees
Oct 18 - Oct 19
The gardners Cottage 1 mile from long Island Sound - pet friendly

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (65 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $342
CA $391 total
includes taxes & fees
Oct 22 - Oct 23
North Fork Resort

11. 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.
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

12. 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
9.4 out of 10, Exceptional, (3 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is CA $213
CA $506 total
includes taxes & fees
Oct 20 - Oct 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

13. 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 CA $160
CA $387 total
includes taxes & fees
Oct 28 - Oct 29
Insta-worthy Couples Retreat: Perfect for romantic getaway!

14. 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 $410
CA $806 total
includes taxes & fees
Nov 2 - Nov 3
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

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

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.4 out of 10, Very good, (6 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 $213
CA $412 total
includes taxes & fees
Oct 27 - Oct 28
The Stern at Soundview · Beach+Ocean+Sunrise

16. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (12 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is CA $148
CA $199 total
includes taxes & fees
Oct 19 - Oct 20
The Tiny Cottage & Mini Farm

17. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (27 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is CA $135
CA $362 total
includes taxes & fees
Nov 1 - Nov 2
Harbor Heights

18. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (55 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is CA $135
CA $357 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper

19. 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 $184
CA $325 total
includes taxes & fees
Nov 4 - Nov 5
Walk To Goodspeed Opera House!

20. Grey comfort room

Grey comfort room
New London
9.6 out of 10, Exceptional, (4 reviews)
"Nice place"
United States
JACQUELINE FELICIANO
The price is CA $83
CA $165 total
includes taxes & fees
Oct 21 - Oct 22
Grey comfort room
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 Westbrook Hotel Reviews

Find out more about Westbrook

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 Westbrook. 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.

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Frequently asked questions

Can I find vacation rentals in Westbrook?

Yes, we have vacation rentals close to top sights in Westbrook, or you can go with a secluded option if you're looking for relaxation. Visitors to Westbrook speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the spas and shopping during your trip.

What are some of the best vacation home rentals that Westbrook has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Westbrook vacation home rental. It 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 will I find in Westbrook?

Expedia has 47 vacation rentals for your stay in Westbrook.

What can I see and do in Westbrook?

Explore the area and family-friendly sights such as Essex Steam Train, or get out into nature at a spot like Westbrook Town Beach. In the larger area, you’ll find Tanger Outlets and Chalker Beach.

What are vacation rentals like in Westbrook?

Vacation rentals are private accommodations you can stay in for several days or more in Westbrook. Vacation rentals provide amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.