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

Westbrook Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Westbrook vacation rentals

A beach with waves, a clear sky, and a sandy shore.

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 ￥21,181
￥51,363 total
includes taxes & fees
Oct 7 - Oct 8
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

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 ￥31,440
￥81,218 total
includes taxes & fees
Oct 15 - Oct 16
Adorable Cottage, 5 min walk to water & town
A dining area with a wooden table, white chairs, a checkered tablecloth, a vase with flowers, and a decorative ceiling light.

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)
"Very clean and comfortable"
United States
Francine F.
The price is ￥32,950
￥83,099 total
includes taxes & fees
Oct 4 - Oct 5
Adorable Cottage with Cottage porch, walk to water & town
A beach with waves, a clear sky, and a sandy shore.

4. 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 ￥29,735
￥71,630 total
includes taxes & fees
Oct 7 - Oct 8
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

5. 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 ￥47,796
￥113,726 total
includes taxes & fees
Oct 20 - Oct 21
Beachside Bliss w/ Game Room, Gym & Golf Green
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

6. 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 ￥19,128
￥36,615 total
includes taxes & fees
Oct 5 - Oct 6
1-bedroom cottage with Grove Beach 🏖️ access.
A cabin with a dining table set for two, a bicycle, and a small porch area.

7. 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, (197 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is ￥21,334
￥31,803 total
includes taxes & fees
Nov 2 - Nov 3
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern house with a deck, outdoor seating, and a fire pit.

8. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥38,677
￥44,189 total
includes taxes & fees
Oct 12 - Oct 13
North Fork Resort
A living room with a fireplace, a sofa, a coffee table, and a cabinet.

9. 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, (14 reviews)
"Very clean & comfortable home, great host & location! "
United States
Becky W.
The price is ￥37,769
￥79,070 total
includes taxes & fees
Oct 7 - Oct 8
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
Terrace/patio

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is ￥26,712
￥48,050 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

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 ￥24,795
￥47,131 total
includes taxes & fees
Oct 8 - Oct 9
The gardners Cottage 1 mile from long Island Sound - pet friendly
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

12. 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 ￥45,340
￥88,586 total
includes taxes & fees
Oct 12 - Oct 13
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
A beach with a house in the background, a clear sky, and a calm sea.

13. 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 ￥24,890
￥57,030 total
includes taxes & fees
Oct 20 - Oct 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A stone pier leading to a beach with houses in the background.

14. 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 ￥18,278
￥43,352 total
includes taxes & fees
Oct 14 - Oct 15
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A rocky shoreline with a beach and ocean in the background.

15. 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 ￥23,422
￥45,042 total
includes taxes & fees
Oct 6 - Oct 7
The Stern at Soundview · Beach+Ocean+Sunrise
A large, white, multi-story building with a prominent tower and a flag on top.

16. 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 traveler
The price is ￥21,808
￥37,959 total
includes taxes & fees
Oct 6 - Oct 7
Walk To Goodspeed Opera House!
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

17. 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 ￥16,294
￥21,887 total
includes taxes & fees
Oct 6 - Oct 7
The Tiny Cottage & Mini Farm
A rocky shoreline with a beach and ocean in the background.

18. 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 ￥24,347
￥46,346 total
includes taxes & fees
Oct 4 - Oct 5
Freeboard at Soundview · Beach+Ocean+Sunrise
A rocky shoreline with a beach and ocean in the background.

19. 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 ￥24,347
￥46,346 total
includes taxes & fees
Oct 4 - Oct 5
The Mast at Soundview · Beach+Ocean+Sunrise
A two-story house with a front porch, a balcony, and a driveway.

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 ￥8,501
￥17,451 total
includes taxes & fees
Oct 5 - Oct 6
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

Inn at Middletown

Inn at Middletown

10/10 Excellent
"Met my expectations and breakfast was wonderful!"
Dorothy 2-night trip
Posted 4 hours ago
Inn at Middletown

Find out more about Westbrook

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

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

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.