Holiday Rentals Westbrook from £90: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Westbrook holiday 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

Westbrook Center

Mason T.

includes taxes & fees

19 Oct - 20 Oct

A living room with a sofa, armchair, coffee table, and a television.

2. Westbrook Getaway-Near Beaches, Train & Shoreline

Westbrook Center

includes taxes & fees

20 Oct - 21 Oct

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

Westbrook Center

Francine F.

includes taxes & fees

18 Oct - 19 Oct

An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

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

Westbrook

Shannon G.

includes taxes & fees

18 Oct - 19 Oct

5. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

Westbrook Center

Dorothy W.

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

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

Clinton

JM B.

includes taxes & fees

21 Oct - 22 Oct

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

East Haddam

Stephanie

includes taxes & fees

16 Nov - 17 Nov

8. Cliffside Resort Condominiums

Greenport

William

includes taxes & fees

12 Nov - 13 Nov

A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

9. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Mary S.

includes taxes & fees

18 Oct - 19 Oct

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

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

Old Saybrook

Karol T.

includes taxes & fees

18 Oct - 19 Oct

A modern house with a deck, outdoor seating, and a fire pit.

11. North Fork Resort

Greenport

Harold

includes taxes & fees

2 Nov - 3 Nov

A stone pier leading to a beach with houses in the background.

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

Old Lyme

Emily M.

includes taxes & fees

28 Oct - 29 Oct

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!

Madison

Samantha D.

includes taxes & fees

20 Oct - 21 Oct

A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

14. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Saybrook Manor

Alexis L.

includes taxes & fees

2 Nov - 3 Nov

A rocky shoreline with a beach and ocean in the background.

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

Old Lyme

"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."

Janine

includes taxes & fees

18 Oct - 19 Oct

A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

16. The Tiny Cottage & Mini Farm

Oakdale,

Jeffrey H.

includes taxes & fees

20 Oct - 21 Oct

A large, white, multi-story building with a prominent tower and a flag on top.

17. Walk To Goodspeed Opera House!

East Haddam

Anonymous traveller

includes taxes & fees

3 Nov - 4 Nov

A beach with people relaxing on chairs and sunbathing.

18. Harbor Heights

Pipes Cove

Steven R.

includes taxes & fees

2 Nov - 3 Nov

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

19. Aqua Vista

Pipes Cove

Kerri L.

includes taxes & fees

9 Nov - 10 Nov

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Top Westbrook Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Very clean bathroom. Very dated and weathered furniture. The linens were good. The paint on the door needed cleaned. The receptionist was very personable. We were on the first level and could hear the folks above."

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Cabins in the woods by Bonvoy Marriott. Who knew? What a great spot- truly amazing, driving up the east coast, having this jewel of a property pop up. I’ll be researching how this was developed, and where they can sneak more little cabins into beautiful forests."

Inn at Middletown

8/10 Good

"We stayed for one night. The location is very convenient and within walking distance to quite a lot in the area. We had valet parking which was very nice since parking for the hotel is down the street. We had dinner and breakfast at the hotel restaurant. It was very good and the waitstaff very attentive. However, when we sat down for dinner the water glasses were filthy. Mine had old lipstick marks all around the edges and his was just plain dirty. Needless to say we asked for clean glassware. We had drinks in the bar. We were disappointed that they had a "Girl's Fun Night Out" thing going on in the bar they had psychic's there. We were not aware of it when we booked and it was very crowded in the bar. It took awhile to get drinks because they only had one barmaid working there. The drinks are too high! $20 for a tequila sunrise. We had 2 drinks and a beer and it cost us $45.00 not including the tip. Just be aware before you order to ask the price first! The room was large and clean. It was a handicap accessible room, however the sliding bathroom door is very heavy and hard to slide. The curtains in the room.... were actually dry rotted and had several holes. Room 117 if the hotel is reviewing this. I think for a high end hotel they can do better. We were not horribly disappointed but would not stay there again."

Find out more about Westbrook

Everything you need to know about Westbrook holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westbrook holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westbrook holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westbrook holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westbrook. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westbrook holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westbrook holiday rentals we have selected for you start as low as £90 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Westbrook rentals

At Expedia, we put the best Westbrook holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Westbrook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westbrook holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westbrook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Westbrook 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 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 Chalker 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.

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Check prices for these dates

Our top choices for Westbrook holiday rentals

1. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

2. Westbrook Getaway-Near Beaches, Train & Shoreline

3. Adorable Cottage with Cottage porch, walk to water & town

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

5. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

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