Westbrook Vacation Rentals from $121: Search Short-Term Rentals

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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

Westbrook Center

Mason T.

$252 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

Westbrook Center

Donovan V.

$393 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

Kevin K.

$436 nightly

Sep 30 - Oct 1

Total with taxes and fees

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.

$518 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

Westbrook Center

Dorothy W.

$330 nightly

Sep 29 - Sep 30

Total with taxes and fees

A cabin with a dining table set for two, a bicycle, and a small porch area.

6. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Melissa

$175 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

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

Clinton

JM B.

$199 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

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

Old Saybrook

Becky W.

$397 nightly

Oct 1 - Oct 2

Total with taxes and fees

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.

$253 nightly

Oct 7 - Oct 8

Total with taxes and fees

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

10. 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

$225 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

11. The Tiny Cottage & Mini Farm

Oakdale,

Angela A.

$124 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

12. North Fork Resort

Greenport

Harold

$222 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

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

Old Lyme

Emily M.

$232 nightly

Sep 30 - Oct 1

Total with taxes and fees

A beach with a house in the background, a clear sky, and a calm sea.

14. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

$291 nightly

Oct 6 - Oct 7

Total with taxes and fees

A rocky shoreline with a clear view of the ocean and a distant shoreline with buildings.

15. Keel at Soundview · Beach+OceanView+Sunrise

Old Lyme

Joseph O.

$238 nightly

Sep 29 - Sep 30

Total with taxes and fees

16. Cliffside Resort Condominiums

Greenport

Christine

$333 nightly

Oct 25 - Oct 26

Total with taxes and fees

A hotel room with two beds, each with patterned bedding, a bedside table with a lamp, and a wall-mounted phone.

17. Cozy 2 Full Beds Micfridge Parking

Branford

$85 nightly

Sep 29 - Sep 30

Total with taxes and fees

A parking lot with a large blue sign indicating a number 6.

18. Cozy 1 King Bed | Smoking

Branford

$82 nightly

Oct 12 - Oct 13

Total with taxes and fees

A reception desk with a staff member, a guest, and a child.

19. Cozy 1 King Bed | Non-Smoking

Branford

$82 nightly

Oct 12 - Oct 13

Total with taxes and fees

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

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

Saybrook Manor

Alexis L.

$466 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Westbrook Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"It is an older property that is very well maintained - the staff could not be more friendly and accommodating. This is coastal CT and hotel prices can be extremely high and there are plenty of options at those price-points - it is nice to find the rare property where “older”, can be clean and comfortable - thank you to the staff!"

North Fork Resort

8/10 Good

"We enjoyed our stay. The cabin was clean a few areas of feedback is that the hot water was lackluster. We had many periods of no hot water. The light fixture was very bright in the sitting area. It would’ve been nice if they had a light dimmer so we didn’t have to unscrew the bulbs. One bulb made the room shine. We were impressed that during the storm we received a phone call asking us if we wanted to relocate to another cabin that was not near trees and in the open area. We appreciate that they took the time to extend the offer. We were also impressed that they came around to pick up the fallen branches and used leaf blower to blow off the leaves and sticks on our porch. We would consider reserving in the summer a week to explore the area. Thank you."

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"It was AMAZING! What a perfect place to reconnect with your partner. We had everything we needed and with the nor’easter, we were cozy up, having a few glasses of wine and playing games and cooking together. We can’t wait to come back! The place was clean, safe, and not a far drive from home."

Find out more about Westbrook

Everything you need to know about Westbrook vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Westbrook vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westbrook vacation 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 low season months. For more hustle and bustle, you may prefer to visit Westbrook in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Westbrook rentals

At Expedia, we put the best Westbrook vacation 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 vacation.

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.

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Things to do in Connecticut

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.

Westbrook Vacation Rentals

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Check prices for these dates

Our top choices for Westbrook vacation rentals

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

2. Adorable Cottage, 5 min walk to water & town

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. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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

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

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

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

11. The Tiny Cottage & Mini Farm

12. North Fork Resort

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

14. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

15. Keel at Soundview · Beach+OceanView+Sunrise

16. Cliffside Resort Condominiums

17. Cozy 2 Full Beds Micfridge Parking

18. Cozy 1 King Bed | Smoking

19. Cozy 1 King Bed | Non-Smoking

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

Find vacation rentals that suit your style

Top Westbrook Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Find out more about Westbrook

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