Westbrook vacation rentals

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

4.89 out of 5 average rating, 204 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

Free onsite parking for 1 car. Beautiful coastal décor and modern amenities makes this a perfect choice for your vacation. Walking distance to EVERYTHING! Dock Square is a 1 minutes walk. Music, Art and Fine Dining surrounds you. Lots of windows and a slider to the deck make this location bright and airy 2 private decks for your enjoyment, two bedrooms, 2 full bathrooms. Perfect for couples or families. Parking for one car in lot, added public park across s NO PARTIES Pets considered

Condo in Old Orchard Beach

A sandy pathway is bordered by tall grasses, leading directly to a calm blue ocean. The serene waters meet a light sky, creating a tranquil scene that suggests easy access to the beach.

4.73 out of 5 average rating, 118 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

nestled in a restful pine grove just 50 feet from Maine’s finest beach. These 8 one & two bedroom charming Old Orchard Beach Cottages are decorated in a modern beach theme, providing guests with the modern conveniences of today. Conveniences include Smart TVs with Amazon Fire Sticks, Wi-Fi, individually controlled heat & air conditioning, fully equipped efficiency kitchenettes, & private baths. Ideal for group getaways! Enjoy the privacy of your own seaside cottage, oh, so close to the beach.

4.98 out of 5 average rating, 330 reviews

A wooden dock extends over vibrant green marshland, leading to a serene body of water. Lush trees and rolling grass create a peaceful backdrop, emphasizing the natural beauty of the surroundings.

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

4.94 out of 5 average rating, 126 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.89 out of 5 average rating, 302 reviews

The A-frame cabin features a wooden deck supported by a sturdy frame, providing access to outdoor seating and a hot tub. Large windows offer views of the surrounding trees, while a snow-covered ground adds to the tranquil winter setting.

Tiny home in Harrison

Million $ views, Hot Tub, Crooked River- Private

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

5 out of 5 average rating, 3 reviews

A charming cottage is nestled among vibrant trees, displaying shades of orange and yellow. Outdoor seating is provided by several blue chairs arranged on a manicured lawn, with a pathway leading to a sunroom that features numerous windows allowing natural light to flood the space.

Home in Wells

"In Tempore" Cottage

Relax in this calm, stylish space. New for 2024, "In Tempore Cottage" at Summer Village! Downtime at the right time! Enjoy the many amenities: tennis, pickle ball, putting green, ball fields that provide unobstructed stargazing on clear nights, heated pools, hot tub, indoor gym, playground. Ride the resort trolley in season. Bike, or walk along peaceful forests. New! Discounted rates for fall! **Linens and towels not included. Guests must supply their own or rent from Cottage Linens**

Townhouse in Kennebunkport

A sandy beach scene is captured, featuring colorful kayaks arranged neatly in the foreground. Sunbathers and beachgoers enjoy the sunny weather, with umbrellas dotting the shoreline. A smooth ocean extends to the horizon, framed by a clear blue sky.

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

Apartment in Kennebunkport

A wooden dining table is surrounded by six matching chairs on a spacious deck. A small vase filled with colorful flowers sits at the center of the table. Beyond the deck, trees provide a lush backdrop, with green views extending toward the distant golf course.

4.93 out of 5 average rating, 29 reviews

Charming Kennebunkport

This gorgeous one bedroom apartment features floor-to-ceiling windows overlooking the prestigious Cape Arundel Golf Course and Kennebunk River. With hardwood floors throughout, updated stainless appliances, a private deck with teak furnishings, and views in all directions, this apartment is even more spectacular than the pictures show. If traveling with a larger group, consider booking the downstairs 2 bedroom apartment as well.

4.95 out of 5 average rating, 151 reviews

A colorful Welcome to Kennebunkport sign stands prominently at the bridge entrance. Below, a charming red building on stilts is seen, featuring a conical rooftop. Surrounding structures showcase classic New England architecture, enhancing the coastal charm of the area.

Home in Kennebunk

Quiet cozy cottage close to restaurants, beach

Winter-wonderland, close to skiing and a walk from great dining. In the summer, enjoy the quiet backyard or walk to the beach! No need to find parking, my place is 3/10 of a mile from downtown Kennebunkport and 7/10 of a mile to Gooch's Beach. You will love my place because of the kitchen, the coziness, and the location. My place is good for couples. It has a tempurpedic king-sized bed and a queen sized pull out bed in the living room.

Home in Old Orchard Beach

A small cabin features a welcoming front porch with two red adirondack chairs. The exterior is light-colored with blue shutters and a white door. A wooden ramp and steps provide access, surrounded by grass and shaded by trees, offering a comfortable entrance to the space.

4.86 out of 5 average rating, 14 reviews

Peaceful Sun and Fun Cabin-B

Your well needed relaxing and peaceful getaway awaits in this newly renovated cabin centrally located on a quiet safe street with short walk to the beach, restaurants, and Pier and amusements. This newly renovated 1-bedroom cozy cabin is perfect for a those looking to spend a peaceful and lovely time near the white sand in Old Orchard Beach. There is a hiking trail and biking trail beginning at the end of our street.

4.83 out of 5 average rating, 139 reviews

A bright dining area features a large glass table surrounded by six black wooden chairs. Natural light filters through three large windows, and a simple floral centerpiece sits at the table's center. A modern chandelier hangs above, complementing the neutral-toned walls.

Apartment in East End

Fall in LOVE With PORTLAND, MAINE

Portland and its surrounding areas is a FOODIE's paradise. Our comfortable home is perfect for Family or Friends to enjoy Portland's charm. Approx 3 miles from Portland Jetport and 90 miles from Boston Logan airport. Walk to downtown or the Old Port on the waterfront. The surrounding areas offer fine beaches and beautiful scenic towns guaranteed to make you want to come back and visit this best kept secret again!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

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A space thats all yours, with room for everyone

Popular amenities for Westbrook vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Westbrook's top sights

The Maine Mall86 locals recommend

Maine Mall86 locals recommend

Bull Jagger Brewing Company38 locals recommend

Mast Landing Brewing Company30 locals recommend

Hannaford Supermarket27 locals recommend

Vena's Fizz House27 locals recommend

Other great vacation rentals in Westbrook

4.93 out of 5 average rating, 58 reviews

A modern kitchen is highlighted with sleek white cabinets and a polished granite countertop. High-end stainless steel appliances, including a gas range, are featured. The open layout connects to a bright living area, where natural light fills the space through large windows.

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

4.93 out of 5 average rating, 121 reviews

A wooden dock extends into a serene body of water, surrounded by lush greenery. Two comfortable chairs are positioned on the dock, with small tables holding drinks. The still water reflects the vibrant colors of the trees, creating a peaceful outdoor setting.

Home in Limerick

Lakefront Getaway

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

4.96 out of 5 average rating, 250 reviews

Home in Lebanon

Tranquility, Relaxation, Family, Romance

4.75 out of 5 average rating, 20 reviews

A covered porch features a comfortable seating area with a wicker sofa and matching cushions, arranged around a low coffee table. A hammock is suspended for relaxation, and a striped outdoor rug adds texture to the wooden floor. Large windows provide views of the surrounding landscape.

Home in Otisfield

Log Cabin *15 acres*hunting* snowmobile*skiing

Home in Old Orchard Beach

A bright kitchen space showcases white cabinetry and stainless steel appliances. A large island with granite countertops features seating for three, complemented by pendant lighting. An adjacent dining area is visible with a table designed for six, creating an open, inviting environment.

4.98 out of 5 average rating, 89 reviews

Woods Lane Golf and Beach Vacation

4.96 out of 5 average rating, 145 reviews

Home in Shapleigh

Secluded Lakehouse/2 private docks*Hottub*big yard