Westbrook vacation rentals

We found 412 vacation rentals — enter your dates for availability

Select from 46 homes, 23 cottages, and other vacation rentals in Westbrook to find one that's perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the amenities you expect for your stay, which might include a pool and a washer and dryer. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Westbrook

Showing deals for:Nov 14 - Nov 21

Image gallery for The little Chestnut. A charming historic apartment in Downtown Chester

Entrance is on the front of the building.
10 out of 10 rating
Exceptional
(5 reviews)

The little Chestnut. A charming historic apartment in Downtown Chester

Chester, CT

10% off
Price is CA $273
CA $2,587 total
includes taxes & fees
The little Chestnut. A charming historic apartment in Downtown Chester

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Find out more about Westbrook

Find out more about Westbrook

Why visit Westbrook

  1. Stunning Beaches: Westbrook boasts beautiful sandy shores, perfect for sunbathing and beach activities.
  2. Outdoor Adventures: Enjoy hiking and exploring nearby national and state parks, ideal for nature enthusiasts.
  3. Charming Cottages: Experience rustic seaside living with cozy accommodations that enhance your getaway.
  4. Family-Friendly Atmosphere: Westbrook caters to families, offering a range of activities for all ages.
  5. Fascinating Railway Museum: Discover the area's history and rail heritage at the local museum.

Popular types of accommodation in Westbrook

Explore the charm of Westbrook with a variety of vacation rentals that cater to every traveler's needs. From cozy cottages and spacious houses to convenient apartments, you'll find the perfect spot for your getaway. Whether you're seeking Westbrook cottage rentals or holiday cottages, our platform ensures transparency and savings, so you can focus on enjoying your stay. Discover the ideal Westbrook vacation rentals and create unforgettable memories in this delightful destination.

  • Houses: These are the top choice for visitors to Westbrook, offering spacious and comfortable lodging for families, friends, or couples.
  • Cottages: A close second, cottages provide a charming and quaint atmosphere, perfect for those seeking a cozy getaway.
  • Apartments: Ideal for individuals or smaller groups, apartments offer convenience and amenities in a home-like setting.
  • Condos: A popular choice for those who enjoy resort-style living with shared amenities and easy access to local attractions.
  • Villas: These luxurious options provide an upscale experience, ideal for relaxing in style during your stay.**

Top attractions in Westbrook

Westbrook, Connecticut, is an ideal destination for a romantic and scenic getaway, offering a variety of outdoor activities. Visitors can explore stunning beaches, the nearby national/state parks, and the fascinating railway museum. This charming locale caters to those seeking cultural experiences, beach fun, and nature adventures, making it perfect for families, couples, or solo travellers looking to immerse themselves in its beautiful surroundings.

  1. Hammonasset Beach State Park: This expansive park features stunning coastal scenery, offering a range of outdoor activities such as hiking, biking, and picnicking. With its sandy beaches and picturesque views, it's perfect for adventure seekers and nature lovers alike.
  2. Harvey's Beach: A charming beach known for its relaxing atmosphere, Harvey's Beach is ideal for sunbathing and swimming. Its family-friendly vibe makes it a great spot for a leisurely day by the water.
  3. Essex Steam Train: Step back in time at this railway museum, where you can explore the rich history of steam trains. The scenic rides provide a unique cultural experience, complete with picturesque views of the Connecticut River.

Things to do recommended for couples

Discover romance in Westbrook, Connecticut! Visit Chamard Vineyards for a delightful wine tasting, savour a meal at Anna Mia's with its inviting atmosphere, or enjoy some fun at Shelter Island Whale's Tail mini-golf. Each experience offers a unique way to connect as a couple!

Things to do recommended for families

On your family vacation in Westbrook, enjoy the thrills at Stay and Play LLC, the adventure-filled arcade just 4.8km away. Explore the outdoor fun at Devil’s Hopyard State Park, 12.9km away, or relax at the family-friendly Ocean Beach Park, situated 112.9km from Westbrook.

Things to do recommended for groups

Groups visiting Westbrook can enjoy shopping at the Clinton Crossing Premium Outlets, catch a show at the Ivoryton Playhouse for a taste of local culture, and browse unique items at Saybrook Country Barn, all within a convenient 6.4km radius.

What do I need to keep in mind when booking a vacation in Westbrook

If you're planning a trip with friends, family, pets, or if you're seeking extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful booking tips for Vrbo.

  • Traveling to Westbrook with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily apply filters for all of these options, and more, on Vrbo.
  • Traveling to Westbrook with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Westbrook: For many families, a getaway isn't truly fulfilling unless their furry companion is along for the adventure. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Westbrook: If you’re searching for vacation rentals with discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-appointed kitchen, or a private pool in your search as well.

Where to stay in Westbrook

Westbrook, Connecticut, offers a delightful blend of outdoor adventures and romantic scenery, perfect for a memorable vacation. Explore charming cottages and enjoy rustic seaside living with stunning views. The area's family-friendly atmosphere ensures a relaxing retreat, while nearby cities provide a vibrant mix of friendly people and budget-friendly options. Whether you're seeking recreation or a peaceful getaway, Westbrook and its surrounding regions promise an unforgettable travel experience.

  • Old Saybrook: Located a mere 6.4km from Westbrook, Old Saybrook is a charming city that offers a delightful mix of outdoor activities and scenic beauty. This picturesque coastal town is known for its romantic atmosphere, making it a popular destination for couples. Visitors can indulge in various recreational activities, including golfing and exploring the local beach and lake. The nearby casino adds an exciting touch to the experience, while the area's natural landscapes provide perfect spots for relaxation and enjoyment.
  • Greenport: Approximately 20.9km away from Westbrook, Greenport is a vibrant city that draws tourists in with its stunning beaches and outdoor experiences. Known for its romantic allure, this coastal gem offers plenty of activities, such as music concerts and golfing. Visitors can unwind at the family-friendly beaches or take part in events held at local conference venues. The lively atmosphere and diverse attractions make Greenport a must-visit for those looking to soak in the sights and sounds of the beautiful coastline.
  • Old Lyme: Situated 11.3km from Westbrook, Old Lyme is a city that embraces adventure and outdoor exploration. This picturesque locale is ideal for nature lovers, featuring recreational areas, beautiful beaches, and a national state park. The town also hosts music concerts and has a nearby casino for those seeking entertainment. With its scenic vistas and abundance of activities, Old Lyme is perfect for travelers looking to embark on a memorable journey surrounded by nature.

Best time to go to Westbrook

If you're planning a trip to Westbrook, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnyAverageModerately Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageModerately Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageModerately Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnyModerately HighModerately High
July73.8°F (23.2°C)Light RainMostly SunnyModerately HighModerately High
August72.7°F (22.6°C)Light RainMostly SunnyModerately HighModerately High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnyModerately LowAverage
November45.5°F (7.5°C)Light RainMostly SunnyModerately LowAverage
December37.8°F (3.2°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save some money on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to assist you in finding the best options!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform where you can plan new adventures, keep your existing plans on track, or manage your bookings effectively. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The beachside setting of Westbrook is ready to explore

The beaches and other outdoor surroundings create an inviting atmosphere in Westbrook. Travelers like the spas, restaurants and shopping in this relaxing and welcoming city. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Westbrook

Are you searching for attractions to visit during your stay? Venture out of your cozy vacation rental and check out everything that makes Westbrook a fun place to get away. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Chamard Vineyards (5.1 mi / 8.2 km)
  • Chatfield Hollow State Park (9.3 mi / 14.9 km)
  • Kontokosta Winery (12.6 mi / 20.2 km)
  • Machimoodus State Park (14.6 mi / 23.5 km)
  • Gardiner's Bay Country Club (14.8 mi / 23.7 km)
  • Sparkling Pointe (15.5 mi / 24.9 km)

Exploring the natural features in Westbrook

Whether you're looking for adventure or just want to spend some time taking in the scenery, Westbrook is a great spot to appreciate mother nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Westbrook Town Beach (0.7 mi / 1.1 km)
  • Harvey's Beach (2.9 mi / 4.7 km)
  • Clinton Town Beach (3.9 mi / 6.2 km)
  • Hammonasset Beach (5.6 mi / 9.1 km)
  • Goose Island (6.2 mi / 10 km)
  • Chatfield Hollow State Park (9.3 mi / 14.9 km)

Seasonal weather in Westbrook

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 70°F.

How to get to and around Westbrook

Fly into New London, CT (GON-Groton - New London), the closest airport, located 21.1 mi (34 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Fishers Island, NY (FID-Elizabeth Field), which is 21.9 mi (35.2 km) away.

Frequently asked questions

What is the best area to stay in Westbrook when booking a vacation rental?
When considering a vacation rental in Westbrook, Connecticut, the most appealing area is the shoreline. This coastal region offers a delightful mix of scenic beauty and local charm. Staying near the beach not only provides easy access to the sandy shores but also places you in proximity to various attractions.

One top point of interest is the Westbrook Town Beach, superb for sunbathing, swimming, and family picnics. Additionally, the nearby Salt Island, with its tranquil natural surroundings, is an ideal spot for kayaking and exploring the coastline. The area is known for its pleasant atmosphere and community spirit, making it a relaxing getaway.
How much does it cost to rent a vacation home in Westbrook?
Prices for vacation rentals in Westbrook vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Westbrook to more spacious homes.
Are there any discounts for Westbrook vacation house rentals?
You can find great discounts on house rentals in Westbrook on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Westbrook?
For renting a beach house in Westbrook, Connecticut, the shoreline offers some delightful options. The area around Westbrook Town Beach is particularly appealing, as it provides easy access to the sandy shore and beautiful views of Long Island Sound. Many properties in this vicinity come equipped with amenities such as private decks, outdoor grills, and spacious living areas, ideal for families or groups looking to enjoy a beach getaway.

Further along the coast, the Old Salt Farm neighbourhood features charming homes that often include features like large gardens, fire pits, and proximity to both the beach and local shops. This area allows for a relaxed atmosphere with easy access to local dining options and markets, making it convenient for travellers.
What is the most popular type of vacation rental accomodation in Westbrook?
In Westbrook, vacation houses are the most popular rental option, with around 34 available throughout the area. These houses typically offer spacious living areas, fully equipped kitchens, and outdoor spaces such as decks or gardens, making them ideal for families or groups looking to enjoy a home-like experience. Additionally, there are about 21 charming cottages that provide a more intimate setting, often featuring rustic decor and cosy atmospheres. For those seeking a more compact option, several apartments and condos are also available, providing convenient amenities and proximity to local attractions.
Are there any family house rentals in Westbrook?
In Westbrook, Connecticut, there are numerous family-friendly house rentals available, with around 36 options to choose from. This charming coastal town, located along the picturesque shoreline, offers a variety of accommodations that cater to families. Many homes feature spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces superb for children to play and explore.

Visitors can discover properties close to local attractions such as the lovely Westbrook Town Beach and the nearby shopping at the Westbrook Outlets. The area is also known for its beautiful parks and nature trails, which provide ample opportunities for outdoor activities like hiking and picnicking.
Can I rent a vacation home with a pool or hot tub in Westbrook?
In Westbrook, Connecticut, there are several vacation homes available for rent that feature pools and hot tubs. This charming coastal town is known for its beautiful beaches and scenic views, making it an excellent choice for a relaxing getaway. Many of the properties offer amenities such as private pools, outdoor patios, and spacious living areas, great for families or groups looking to unwind. Additionally, fully equipped kitchens are commonly found, allowing guests to prepare meals at their leisure.
Can I find long-stay vacation rentals in Westbrook?
A long-stay vacation rental in Westbrook is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Westbrook?
In Westbrook, Connecticut, there are some pet-friendly house rentals available, with a selection of around 21 options for travellers to choose from. These vacation homes often feature amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, making them ideal for families or groups travelling with pets.
Are there any remote work vacation rentals in Westbrook?
In Westbrook, Connecticut, there are ample options for remote work vacation rentals, with around 54 properties available. This charming coastal town offers a blend of relaxation and productivity, making it an ideal spot for those looking to work remotely while enjoying a picturesque setting. Many of these rentals come equipped with essential amenities for remote work, such as high-speed Wi-Fi, dedicated office spaces, and comfortable desk chairs, ensuring a conducive environment for business tasks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Westbrook vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Westbrook with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Westbrook?
In Westbrook, popular vacation rental amenities include well-equipped kitchens, which typically feature essential appliances such as microwaves and stovetops, along with cookware, dishware, and utensils for preparing meals. This makes it convenient for guests to enjoy home-cooked meals during their stay. The availability of these amenities caters to travellers looking for a comfortable and self-sufficient living space while they explore the charming coastal town and its nearby attractions.
When is the best time to visit Westbrook for a vacation rental?
The most popular time to visit Westbrook for a vacation rental is during the summer months of June to August. This peak season draws families and beachgoers alike, eager to soak up the sun along the picturesque Connecticut shoreline. With warm temperatures averaging around 26-30 degrees Celsius, it's superb for outdoor activities such as swimming, kayaking, and exploring the charming coastal towns.

July is particularly bustling, as visitors flock to enjoy various local events, including summer concerts and vibrant festivals. The lively atmosphere is complemented by the aroma of fresh seafood from nearby eateries, making it an enticing time for those looking to indulge in the local cuisine.

For travellers who prefer a quieter experience while still enjoying pleasant weather, consider visiting in September. The crowds begin to thin, yet the temperatures remain mild, typically in the low 20s Celsius. This transitional month allows visitors to relish the beauty of the changing season, with fewer tourists and a relaxed pace—ideal for leisurely strolls along the beach or exploring the nearby nature trails.
How early should I book a Westbrook vacation rental?
Book your Westbrook vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Westbrook?
In Westbrook, Connecticut, visitors can enjoy a variety of attractions that showcase the town's coastal charm and natural beauty. The Westbrook Town Beach is a popular spot for sunbathing and swimming, offering picturesque views of Long Island Sound. Nearby, the scenic Hammonasset Beach State Park in Madison provides extensive sandy shores and walking trails, superb for a day of outdoor activities.

For those interested in shopping and dining, the Westbrook Outlets features a range of stores and eateries, making it a great destination for both locals and visitors. The town is also home to several marinas, where boating and fishing enthusiasts can indulge in their favourite pastimes while enjoying the serene waters.
Can I change or cancel my Westbrook home rental booking on Vrbo?
To find Westbrook vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Westbrook vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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