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Westbrook, ME vacation rentals
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Best Vacation rentals and Airbnb offers in Westbrook, ME

Top-Rated Vacation Rentals near the City Center in Westbrook, ME

These vacation rentals in the downtown area of Westbrook, ME offer unbeatable walking access to vibrant local life, dining, and culture.

Peaceful 1br | Reading Nook | Near Portland - Westbrook, ME
10 1 review

Peaceful 1br | Reading Nook | Near Portland

apartment, Westbrook
This second-floor residence in Westbrook is located on a quiet, dead-end street, offering a private retreat within a 12-minute walk to downtown Westbrook's shops, restaurants, and the Westbrook River Walk.
This 4-guest capacity apartment, situated in a renovated 1890s home, features air conditioning, internet, a kitchen with a fridge and microwave, and on-site parking, with a dedicated workspace and complimentary coffee and tea available.
Peaceful 1br | Reading Nook | Near Portland - Westbrook, ME
9.9 151 reviews

Peaceful 1br | Reading Nook | Near Portland

apartment, Westbrook
This one-bedroom apartment is located on Pleasant Street in Westbrook, just a short drive from the bustling city of Portland. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment has a modern bathroom, a well-equipped kitchen with granite countertops, and a comfortable living area with a Smart TV. It comfortably sleeps four guests and offers amenities like off-street parking, air conditioning, and high-speed internet.
Private 2 Bedroom Ranch In Frenchtown - Westbrook, ME
9.2 36 reviews

Private 2 Bedroom Ranch In Frenchtown

apartment, Westbrook
This private ranch home is located in a quiet Westbrook neighborhood, just 10 minutes from Portland Jetport and 15 minutes from downtown Portland. Guests consistently rate the home highly for its cleanliness, location, and overall experience.
The two-bedroom home comfortably accommodates up to six guests. Enjoy modern amenities like a fully equipped kitchen, air conditioning, a private garden, and parking.
20 Min 2 Portland | Deck, Grill & Firepit | Dogsok - Westbrook, ME
10 39 reviews

20 Min 2 Portland | Deck, Grill & Firepit | Dogsok

apartment, Westbrook
This Conant Street rental in Westbrook, Maine is a short walk from downtown Westbrook, 15 minutes from Portland, and 25 minutes from Willard Beach.
This 1500-square-foot, three-bedroom home sleeps up to eight guests and features a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, a fire pit, and family-friendly amenities like a pack 'n play and high chair.

Best Westbrook, ME vacation rentals with air conditioning

Garden View Retreat - Westbrook, ME
No reviews

Garden View Retreat

apartment, Westbrook
This two-bedroom rental unit in Westbrook offers a quiet escape surrounded by woods, located just a 15-minute drive from downtown Portland.
Guests can enjoy a private apartment with a spacious kitchen and living area, a large deck with garden and wildlife views, and access to walking, biking, and hiking trails, with a capacity for two people and pets allowed.
Charming 2-bedroom Back Cove Retreat - Westbrook, ME
10 95 reviews

Charming 2-bedroom Back Cove Retreat

apartment, Portland
This two-bedroom, one-bathroom apartment rental is located in Portland, Maine, eight minutes from downtown and steps from Payson Park and the Back Cove trails.
The 4-guest unit features a fully equipped kitchen, in-unit laundry, air conditioning, off-street parking, a private entrance, and family-friendly amenities including a pack 'n play, highchair, and baby gate.
Cozy King Bed Apt Near Portland With Free Parking - Westbrook, ME
9.8 150 reviews

Cozy King Bed Apt Near Portland With Free Parking

apartment, Westbrook
This Westbrook studio apartment is located in a quiet Portland neighborhood, conveniently close to I-95 and I-295, offering easy access to Downtown Portland, Downtown Westbrook, Maine Medical Center, and the Portland International Jetport.
The second-floor unit features a queen-size bed, full kitchen with fridge, freezer, and microwave, a smart TV, dedicated workspace, and accommodates two guests, with free parking and easy self check-in; significant discounts are available for weekly and monthly stays.
Near Portland Trails: Walkable Apartment W/ Deck - Westbrook, ME
No reviews

Near Portland Trails: Walkable Apartment W/ Deck

house, Portland
This Portland apartment is conveniently located near Portland Trails, 2.7 miles from the Portland Observatory, and 3 miles from Merrill Auditorium, offering easy access to Portland's attractions.
This 1000-square-foot house features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, free Wi-Fi, a flat-screen TV, and air conditioning.

Frequently Asked Questions about vacation rentals in Westbrook, ME

  • What are the top family-friendly attractions in Westbrook, ME?

    The Westbrook Community Center offers a variety of programs and activities for families, including swimming, fitness classes, and youth sports. The nearby Riverwalk Park is also a great place for a family picnic or to enjoy a leisurely stroll along the Presumpscot River.
  • What are the best Airbnb and vacation rentals in Westbrook, ME?

  • When is the best time to book a vacation rental in Westbrook, ME?

    The best time to book a vacation rental in Westbrook is during the shoulder seasons, from April to May or September to October. You'll avoid the crowds and enjoy milder weather. Of course, if you're looking for a more festive atmosphere, you can always book during the summer months for the Westbrook Farmers Market and other events.
  • What are the most popular Airbnbs in Westbrook, ME?

  • What events or festivals should visitors check out in and around Westbrook, ME?

    The Westbrook Farmers Market, held every Saturday from June to October, is a great way to experience local food and crafts. The annual Riverfest, held in August, features live music, food, and family-friendly activities.
  • What are the best vacation rentals with a pool in Westbrook, ME?

  • What are the best budget-friendly activities in Westbrook, ME?

    The Riverwalk is a great place to go for a free walk or bike ride, offering beautiful views of the Presumpscot River. You can also check out the public art installations throughout the city, including the sculptures at the Westbrook Community Center.
  • What are the best rentals for families and kids in Westbrook, ME?

  • What are the best restaurants with local dishes in Westbrook, ME?

    The Lobster Shack is a local favorite, serving up fresh seafood, including lobster rolls and clam chowder. For a more casual dining experience, try the Riverwalk Cafe, known for its homemade soups and sandwiches.
  • What are the best rentals or Airbnbs with a jacuzzi in Westbrook, ME?

    Comfortable Home And Yard - Minutes To Portland and Fabulous 3 Bedrooms - 2 Bathrooms And Hot Tub are the best vacation rentals or Airbnb with a jacuzzi in Westbrook, ME.

  • What are the best walking or cycling routes in Westbrook, ME?

    The Riverwalk Trail is a scenic and easy walking or cycling route that follows the Presumpscot River. For a longer ride, you can connect to the Eastern Promenade Trail in Portland, which offers stunning views of the city and the harbor.
  • Are there pet-friendly attractions in Westbrook, ME?

    The Riverwalk is a great place to take your dog for a walk, and many of the restaurants in the downtown area have outdoor seating that is pet-friendly. The Westbrook Community Center also has a dog park.
  • What are the benefits of choosing a vacation rental in Westbrook, ME?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities such as kitchens and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Westbrook, ME?

    The Westbrook Community Center has a variety of sports facilities, including a gymnasium, a swimming pool, and tennis courts. The city is also home to the Westbrook High School, which has a large athletic complex.

Popular destinations

Best Vacation Rentals with Balconies in Westbrook, ME

Enjoy a Westbrook, ME vacation rental with a balcony and stunning city skyline views for a truly memorable stay.

New Luxe Coastal Retreat | Hot Tub & Fire Pit - Westbrook, ME
9.4 10 reviews

New Luxe Coastal Retreat | Hot Tub & Fire Pit

apartment, Portland
This luxurious 4-bedroom, 6-bathroom Portland apartment rental is located in the North Deering neighborhood, a short drive from Falmouth and Casco Bay beaches, offering easy access to Maine attractions like Acadia National Park (within 1-2 hours).
The 2,900-square-foot residence boasts an open-concept design, accommodating up to 10 guests with a gourmet kitchen, private deck overlooking a creek, a 7-person hot tub, and blazing-fast 2 GIG fiber optic internet.
The Woodland Loft At Falmouth - Westbrook, ME
No reviews

The Woodland Loft At Falmouth

house, Falmouth
The Woodland Loft, a house in Pleasant Hill, Falmouth, is located 7.2 miles from Portland Observatory and 8.7 miles from Portland International Jetport Airport.
This air-conditioned vacation home offers 4040 square feet of living space with 2 bedrooms and 1 bathroom, accommodating up to 7 guests with a fully equipped kitchen, free WiFi, and a private entrance, with nearby attractions including Funtown Splashtown USA and Aquaboggan Water Park.
Great Suburban Location Close To Town! - Westbrook, ME
No reviews

Great Suburban Location Close To Town!

apartment, Portland
This Portland apartment in the Deering Center neighborhood is a 6-minute walk from Westbrook College Historic District and a 4-minute drive from the State Theatre, offering convenient access to local attractions.
This pet-friendly rental accommodates two guests with one bedroom and one bathroom, featuring air conditioning, Wi-Fi, a full kitchen with a fridge and microwave, an in-unit washer/dryer, and on-site parking.
The Coastal Connection - Westbrook, ME
7.6 5 reviews

The Coastal Connection

apartment, South Portland
This 2-bedroom, 1-bathroom apartment in South Portland's Les Hauteurs de Thorton district is a short walk from Casco Bay and a 4-minute drive to Maine Mall, offering easy access to shopping and dining.
This pet-friendly rental accommodates up to 5 guests and features a full kitchen, air conditioning, Wi-Fi, a private garden, and a balcony, with Scarborough Beach State Park and Crescent Beach State Park nearby.

Top Vacation Rentals for Families in Westbrook, ME

Ideal for family vacations, these Westbrook, ME rentals or Airbnbs offer spacious layouts near top city attractions.

Modern Apartment - 20 Mins To Portland, Deck, Grill & Firepit, King Bed, Dogsok - Westbrook, ME
10 12 reviews

Modern Apartment - 20 Mins To Portland, Deck, Grill & Firepit, King Bed, Dogsok

apartment, Westbrook
This spacious Westbrook apartment rental is a 15-minute walk from downtown Westbrook, a 20-minute drive from Portland's Old Port, and 12 minutes from the University of Southern Maine in Gorham.
The 1,500-square-foot three-bedroom, two-bathroom dwelling sleeps up to eight guests and boasts a private deck, gas grill, fire pit, and access to local discounts on kayak/SUP and bike rentals.
Harmony House/walk To Downtown/parking/balcony - Westbrook, ME
10 4 reviews

Harmony House/walk To Downtown/parking/balcony

apartment, Portland
This Portland apartment is located in a residential neighborhood, 8-10 minutes by car from the Old Port and Portland Museum of Art.
This 3-bedroom, 2-bathroom condo accommodates up to 8 guests, offering a full kitchen, high-speed Wi-Fi, a private balcony, and on-site parking.
Bright & Spacious Apartment With Amazing Shower - Westbrook, ME
9.6 862 reviews

Bright & Spacious Apartment With Amazing Shower

apartment, Portland
This apartment is located in Portland's Parkside neighborhood, just a short walk from the waterfront and Deering Oaks Park, offering a peaceful escape from the city's hustle and bustle. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 1-bedroom, 1-bathroom dwelling spans 600 square feet and comfortably accommodates up to 4 guests. Enjoy amenities like a fully equipped kitchen, a washer/dryer, free WiFi, and a Smart TV, along with access to a spa, parking, and a smoke-free environment.
5 Star Back Cove Apartment With Water View! - Westbrook, ME
10 162 reviews

5 Star Back Cove Apartment With Water View!

apartment, Portland
This Back Cove vacation rental is a short walk from Casco Bay and the University of Southern Maine, and within two miles of the Southworth Planetarium and Bayside Bowl.
The 700-square-foot house features one bedroom, one bathroom, and accommodates two guests, offering a fully equipped kitchen, private patio, free Wi-Fi, and a garden with barbecue grills.

Best Westbrook, ME vacation rentals with parking

Majestic Sanctuary!! - Westbrook, ME
9.9 90 reviews

Majestic Sanctuary!!

apartment, Westbrook
Quiet & Cozy Apartment On A Christmas Tree Farm. - Westbrook, ME
10 2 reviews

Quiet & Cozy Apartment On A Christmas Tree Farm.

apartment, Windham
Modern 3br | W/d + Parking | Near Portland - Westbrook, ME
No reviews

Modern 3br | W/d + Parking | Near Portland

apartment, Westbrook
Private Entrance Residential Portland - Westbrook, ME
8.6 8 reviews

Private Entrance Residential Portland

apartment, Portland

Compare Luxury Vacation Rentals in Westbrook, ME

Stay in a luxury city-center vacation rental in Westbrook, ME for a sophisticated urban escape with premium 5-star amenities.

Quaint Farmhouse Master Suite W/private Bath - Westbrook, ME
9.7 93 reviews

Quaint Farmhouse Master Suite W/private Bath

apartment, Westbrook

Our Favorite Pet-Friendly Vacation Rentals in Westbrook, ME

Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Westbrook, ME are steps away from dog parks and city walks.

Sleeps 16+ | W/d | Parking | 15 Mins To Old Port - Westbrook, ME
No reviews

Sleeps 16+ | W/d | Parking | 15 Mins To Old Port

apartment, Westbrook
Good Vibes Portland Home - 4 Wonderful Seasons - Westbrook, ME
9.1 9 reviews

Good Vibes Portland Home - 4 Wonderful Seasons

house, Portland
Maine Coastal Getaway - Westbrook, ME
9.7 23 reviews

Maine Coastal Getaway

apartment, South Portland
Tranquility Between The Lakes & Sea - Westbrook, ME
No reviews

Tranquility Between The Lakes & Sea

apartment, Westbrook

Explore Vacation Rentals with a Pool in Westbrook, ME

Dive into a refreshing stay with these Westbrook, ME rentals and Airbnbs that offer on-site swimming pool access in the heart of the city.

Portland Pool House - Minutes To The Old Port! - Westbrook, ME
10 1 review

Portland Pool House - Minutes To The Old Port!

house, Portland
Gorgeous 3-bedroom House With A Pool In Charming Portland - Westbrook, ME
8.8 3 reviews

Gorgeous 3-bedroom House With A Pool In Charming Portland

apartment, Portland

Search Vacation Rentals with Jacuzzi in Westbrook, ME

Unwind at the end of a busy city day with a private hot tub at these hand-selected vacation rentals in Westbrook, ME.

New Luxe Coastal Retreat | Hot Tub & Fire Pit - Westbrook, ME
9.4 10 reviews

New Luxe Coastal Retreat | Hot Tub & Fire Pit

apartment, Portland
Majestic Sanctuary!! - Westbrook, ME
9.9 90 reviews

Majestic Sanctuary!!

apartment, Westbrook
Apt In Victorian Mansion W/ Hot Tub, Parking, Pool - Westbrook, ME
9.9 512 reviews

Apt In Victorian Mansion W/ Hot Tub, Parking, Pool

apartment, Portland
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