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. 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 $232
CA $664 total
includes taxes & fees
Sep 21 - Sep 22
Adorable Cottage, 5 min walk to water & town

2. 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 $186
CA $455 total
includes taxes & fees
Sep 21 - Sep 22
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

3. 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 $290
CA $737 total
includes taxes & fees
Sep 21 - Sep 22
Adorable Cottage with Cottage porch, walk to water & town

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 $343
CA $905 total
includes taxes & fees
Sep 23 - Sep 24
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 $260
CA $633 total
includes taxes & fees
Sep 21 - Sep 22
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

6. 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, (190 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is CA $180
CA $272 total
includes taxes & fees
Sep 21 - Sep 22
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

7. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (59 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $169
CA $321 total
includes taxes & fees
Oct 6 - Oct 7
1-bedroom cottage with Grove Beach 🏖️ access.

8. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $396
CA $452 total
includes taxes & fees
Oct 19 - Oct 20
North Fork Resort

9. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
The price is CA $385
CA $595 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums

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)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The price is CA $220
CA $398 total
includes taxes & fees
Oct 13 - Oct 14
The gardners Cottage 1 mile from long Island Sound - pet friendly

11. 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 $369 total
includes taxes & fees
Sep 21 - Sep 22
The Stern at Soundview · Beach+Ocean+Sunrise

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
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 $208
CA $468 total
includes taxes & fees
Sep 28 - Sep 29
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

13. 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 $391 total
includes taxes & fees
Sep 21 - Sep 22
Keel at Soundview · Beach+OceanView+Sunrise

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 $403
CA $793 total
includes taxes & fees
Sep 21 - Sep 22
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

15. 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 $206
CA $352 total
includes taxes & fees
Sep 22 - Sep 23
Walk To Goodspeed Opera House!

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

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (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 CA $157
CA $378 total
includes taxes & fees
Sep 29 - Sep 30
Insta-worthy Couples Retreat: Perfect for romantic getaway!

17. Cozy 1-bedroom apartment in peaceful Branford with AC and gym access

Cozy 1-bedroom apartment in peaceful Branford with AC and gym access
Branford
The price is CA $134
CA $250 total
includes taxes & fees
Sep 21 - Sep 22
Cozy 1-bedroom apartment in peaceful Branford with AC and gym access

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 CA $187
CA $373 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

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 CA $161
CA $213 total
includes taxes & fees
Oct 6 - Oct 7
The Tiny Cottage & Mini Farm

20. 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 $169
CA $368 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Lakefront Tiny House
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 Crystal Lake Town Park.

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.