Westbrook Vacation Rentals from $116: Search Short-Term Rentals

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Our top choices for Westbrook vacation rentals

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

Westbrook Center

Donovan V.

$427 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Westbrook

Shannon G.

$510 nightly

Sep 9 - Sep 10

Total with taxes and fees

3. Cozy Lakefront Tiny House

East Lyme

Richard R.

$246 nightly

Sep 9 - Sep 10

Total with taxes and fees

4. Lakefront Boho Tiny House

East Lyme

Annaliaa C.

$225 nightly

Sep 9 - Sep 10

Total with taxes and fees

5. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Morainny

$224 nightly

Sep 9 - Sep 10

Total with taxes and fees

1 bedroom, desk, iron/ironing board, travel crib

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

Clinton

JM B.

$209 nightly

Oct 5 - Oct 6

Total with taxes and fees

7. North Fork Resort

Greenport

Lisa

$270 nightly

Sep 13 - Sep 14

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Clinton

Wink V.

$263 nightly

Oct 7 - Oct 8

Total with taxes and fees

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Top Westbrook Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"Good location. Clean room. Friendly staff. Need towels by the sink. Coffee maker, but no coffee."

Saybrook Point Resort & Marina

10/10 Excellent

"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."

Sound View Greenport

10/10 Excellent

"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city and enjoy some quiet time by the water. Greenport is also nearby, making it convenient to explore the local restaurants, shops, vineyards, and other attractions. If you’re planning a trip to Greenport or the North Fork, Sound View is definitely a place worth considering. I would happily stay here again! 🌅🌊❤️"

North Fork Resort

8/10 Good

"My sisters and I booked a 2 bedroom cottage for a long weekend around Greenport. The listing said it was a 2 bedroom with queen beds but when I arrived I realized one room was only a full so one of us had to sleep on the pull out couch for us all to be comfortable. You also definitely need a car. It’s a 45 min walk from the train station so if you’re coming from the city it’s not a convenient location and it’s off a busy road. The cottage did have lots of kitchen amenities and a grill which is great if you’re looking for some easy meals. The shower’s water pressure was great and the air conditioning was effective. Unfortunately you can’t open any windows because there are no screens in the windows and the area is buggy. Overall, the place was nice but the rooms are smaller than I expected and you’re far from everything (even the main reception and pool)"

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 $116 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.

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Check prices for these dates

Our top choices for Westbrook vacation rentals

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

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

3. Cozy Lakefront Tiny House

4. Lakefront Boho Tiny House

5. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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

7. North Fork Resort

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

9. Cliffside Resort Condominiums

10. The Tiny Cottage & Mini Farm

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

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

13. Walk To Goodspeed Opera House!

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

15. Comfy Waterfront Walkout! Enjoy your own private terrace overlooking the Thames!

16. Chic Groton Studio • Cozy and Modern. Close to Casinos, Navy Base, Mystic & More

Find vacation rentals that suit your style

Top Westbrook Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Saybrook Point Resort & Marina

Regency Inn & Suites New London, Mystic

Water's Edge Resort & Spa

Sound View Greenport

Fairfield by Marriott Inn & Suites Wallingford New Haven

Holiday Inn New London - Mystic Area by IHG

2 mins/350 ft walk to West Beach 4-BR cottage in Westbrook, CT with large yard

North Fork Resort

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