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

Westbrook Holiday Rentals

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Our top choices for Westbrook holiday 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 NZ$689
includes taxes & fees
9 Aug - 10 Aug
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
9.4 out of 10, Exceptional, (16 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is NZ$778
includes taxes & fees
9 Aug - 10 Aug
Adorable Cottage, 5 min walk to water & town

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

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is NZ$1,351
includes taxes & fees
25 Aug - 26 Aug
Beachside Bliss w/ Game Room, Gym & Golf Green

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
The price is NZ$889
includes taxes & fees
31 Aug - 1 Sept
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

5. 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, (175 reviews)
"Beautiful view, very clean !"
United States
Karolyne
The price is NZ$467
includes taxes & fees
10 Aug - 11 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
The price is NZ$409
includes taxes & fees
3 Sept - 4 Sept
1-bedroom cottage with Grove Beach 🏖️ access.

7. 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, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is NZ$558
includes taxes & fees
3 Sept - 4 Sept
The gardners Cottage 1 mile from long Island Sound - pet friendly

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

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is NZ$505
includes taxes & fees
6 Aug - 7 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

9. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (280 reviews)
"Great place!"
United States
Christine
The price is NZ$804
includes taxes & fees
9 Aug - 10 Aug
Cliffside Resort Condominiums

10. 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
The price is NZ$615
includes taxes & fees
2 Sept - 3 Sept
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

11. 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 NZ$543
includes taxes & fees
6 Aug - 7 Aug
Keel at Soundview · Beach+OceanView+Sunrise

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NZ$1,258
includes taxes & fees
17 Aug - 18 Aug
North Fork Resort

13. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
The price is NZ$442
includes taxes & fees
11 Aug - 12 Aug
Walk To Goodspeed Opera House!

14. Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
New London
10.0 out of 10, Exceptional, (13 reviews)
"Parking was easy and the room was the right siz."
United States
Vicente B.
The price is NZ$245
includes taxes & fees
18 Aug - 19 Aug
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

15. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is NZ$584
includes taxes & fees
1 Sept - 2 Sept
Cozy Lakefront Tiny House

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, (139 reviews)
"The house was great for our group of 8. The lister's were very helpful and gracious when one of our members left their wallet behind. We had a lovely time and recommend the property."
United States
Stephanie G.
The price is NZ$1,111
includes taxes & fees
6 Aug - 7 Aug
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

17. Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (2 reviews)
"The home was very clean and welcoming."
United States
Michelle M.
The price is NZ$788
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom house with WiFi, AC in lovely Waterford

18. 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 NZ$374
includes taxes & fees
1 Sept - 2 Sept
Cozy 1-bedroom apartment in peaceful Branford with AC and gym access

19. Grey comfort room

Grey comfort room
New London
10.0 out of 10, Exceptional, (1 review)
"Muy bien servicio"
United States
Eduin Vicente
The price is NZ$189
includes taxes & fees
31 Aug - 1 Sept
Grey comfort room

20. 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, (34 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is NZ$429
includes taxes & fees
2 Sept - 3 Sept
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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 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 Westbrook 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 Westbrook. 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 Westbrook. 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 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 Westbrook short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Westbrook?

Yes, there are holiday rentals close to the most popular sights in Westbrook, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Westbrook has to offer?

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!: This holiday home rental outside of Westbrook is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Westbrook?

Expedia has 47 holiday 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 wider area, you’ll find Tanger Outlets and Harvey's Beach.

What are holiday rentals like in Westbrook?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westbrook. Holiday rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.