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Holiday rentals in Westbrook

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Top-rated holiday rentals in Westbrook

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Guest favourite

Villa in New London

4.96 out of 5 average rating, 24 reviews

Waterfront Holiday Vacation Villa New England

Have fun with the whole family at this stylish VILLA with water (kayak) access to Ocean State Beach Park and a 4 minute drive to the quaint Waterford Beach. This idyllic leisure home has everything you need to enjoy your gateway. SECLUDED setting with 300 ft of waterfront access for kayaking , fishing. Sauna, bicycles, waterfront gazebo with fire pit , basketball hoop and hammocks. All spaces are newly renovated and tastefully decorated. New fully stocked kitchen . Close to Mystic - Foxwoods

Guest favourite

Home in North Fork

4.9 out of 5 average rating, 20 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Guest favourite

Apartment in Norwich

4.97 out of 5 average rating, 118 reviews

The Vacay Villa

The Vacay Villa, just minutes away from Mohegan Sun, Foxwoods and The Spa at Norwich Inn, offers so many amenities you won’t even have to leave the grounds. Private balcony, fireplace, two outdoor pools currently open, year-round access to luxurious hot tub and saunas, small workout room, laundry facilities, pub and upscale restaurant allow for a one-of-a-kind stay at an incredibly affordable price. Why spend hundreds to stay at the area casinos when you can stay in your own private villa?

Guest favourite

Home in Farmington

5 out of 5 average rating, 60 reviews

Lake Escape: Lake Cottage Charm, Lake Front, AC

Direct lakefront access with gorgeous views on a private lake. This beautiful 1930's lakefront cottage was fully renovated and reimagined by its owners in 2021. Custom architectural trim and details can be found throughout blending this homes' heritage with modern amenities. 2 bedrooms, eat-in kitchen and window seat nook, 2 full baths, custom barn doors and cabinetry, a reimagined sunroom, beautiful views on 100' of accessible lake frontage with outdoor patio, 1 mile from town center.

Guest favourite

Home in Westerly

5 out of 5 average rating, 8 reviews

Cozy, summer house near Misquamicut beach

Cozy, recently renovated house, close to everything in a quiet residential neighborhood, house across cemetery. Walking distance to river/marina with the great restaurants. In the morning, get a coffee from Junk Java, lunch from The Pantry . 3 miles from Watch Hill and The Ocean House, 3 miles from Misquamicut Beach, 5 miles from Weekapaug Beach, 15 minutes from Block Island, 10 miles from Foxwoods and 20 from Mohegan casino, 7 miles to Mystic area, 25 minutes to Groton

Guest favourite

Guest house in East Hampton

4.93 out of 5 average rating, 41 reviews

Family-Friendly Lakeside Cottage

Newly renovated lakeside cottage with stunning views. 2 bedrooms with king beds and a pull-out couch, 1.5 bathrooms - 30 second walk to the lake - Fully furnished and equipped - Private rock patio with picnic table and grill - Washer and dryer in unit - Desk for working from home - 2 Kayaks and 2 paddle boards are available for use - Short walk or drive to restaurants, and shops Perfect for romantic getaways, family vacations, or visiting family locally.

Guest favourite

Home in Montauk

5 out of 5 average rating, 6 reviews

Hilltop Bright Home w/New Pool Summer 2024

Home is professionally managed by Montauk Rental Management Group. Your family will be close to everything when you stay at this centrally-located Montauk home. Short drive to Town and Beaches. This home was recently painted and updated, it's clean, bright and the perfect family rental! -4 bedrooms -3 bathrooms -Spacious deck with water views -Outdoor dining & seating -Grill -Peaceful, quiet location perched on a hill Rental Registry 23-780

Guest favourite

Home in Westbrook

4.93 out of 5 average rating, 42 reviews

Private vacation home, close to beach

Welcome the our new Airbnb where serenity & style come together. Enjoy this charming, cozy home. Upon entering, you'll feel immediately relaxed & on vacation. This home is filled with natural sunlight light, large kitchen, stocked with with gourmet cookware & utensils. Outside you'll hear the babbling brook river, private large yard that offers outside patio deck for dining, entertaining or cuddling up by the fire pit.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Home in Montauk

4.78 out of 5 average rating, 9 reviews

Stunning Sunsets & Bay Views

Your family will be close to everything when you stay at this centrally-located place. Walk or bike to Duryeas, Town, or the Harbor! Large yard overlooking the bay, watch the famous Montauk sunsets from your own private hot tub. -4 Bedrooms (Sleeps 12) -5 bathrooms -Bay views -Hot Tub -Deck w/ outdoor dining -Large Yard -Bikes and Beach Gear -Centrally located -Private and secluded

Guest favourite

Home in Montauk

4.9 out of 5 average rating, 42 reviews

Montauk Family Gem: HotTub, Pro Kitchen, Fireplace

Escape to your perfect Montauk getaway! Nestled on a secluded, beautifully landscaped lot at the end of a quiet dead-end street, this recently renovated 4-bedroom, 3.5-bathroom beach house offers the ultimate combination of luxury, comfort, and privacy—just one mile from both Montauk town and the famous Ditch Plain beaches. We are also pet friendly!

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for Westbrook holiday rentals

Free parking on premises

Air conditioning

Stay near Westbrook's top sights

Essex Steam Train & Riverboat60 locals recommend

Westbrook Outlets44 locals recommend

Lobster Landing39 locals recommend

Bill's Seafood Restaurant36 locals recommend

Café Routier29 locals recommend

Ivoryton Playhouse28 locals recommend

Other great holiday rentals in Westbrook

Cottage in Milford

4.83 out of 5 average rating, 12 reviews

Come to Maresol Cottage w/family & friends.

Guest favourite

Home in Montville

4.9 out of 5 average rating, 49 reviews

Hidden Gem Quite Dead-end St Near All Casinos

Guest favourite

Cottage in Guilford

4.99 out of 5 average rating, 124 reviews

"Red House on the Knoll" at Indian Cove

Guest favourite

Bungalow in Old Lyme

4.94 out of 5 average rating, 293 reviews

Pet Friendly Bungalow!!!

Guest favourite

Home in Waterford

4.94 out of 5 average rating, 18 reviews

Summer Beach Cottage Harknes, Ocean Beach N

Guest favourite

Home in Woodmont

4.98 out of 5 average rating, 42 reviews

Beachfront paradise- come, stay, relax!

Guest favourite

Home in Old Saybrook

5 out of 5 average rating, 38 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

Guest favourite

Home in Woodmont

4.93 out of 5 average rating, 14 reviews

Point Beach House

Quick stats about holiday rentals in Westbrook

Total rentals
140 properties
Nightly prices starting at
₹4,245 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore