Discover a selection of 329 vacation rentals in Westbrook, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $153 per night, and houses and cottages are popular options for a stay in Westbrook. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Westbrook
Destination guide

Wind down in Westbrook

Discover one of Connecticut's most picturesque towns and an ample helping of family fun in Westbrook, a laidback community serving up a great base for a getaway to New England. Nestled against the shoreline of Long Island Sound, the area's annual fall foliage display attracts travelers from across the country, although an array of exciting activities and one-of-a-kind attractions ensure a memorable stay can be enjoyed all year round. Once you choose your Westbrook vacation rental, you'll find everything from relaxed beach days and scenic railroad excursions to quaint downtown shopping and numerous foodie hotspots are on the agenda.

Things to do

Iconic experiences near Westbrook

A gateway to stunning New England, Westbrook vacation rentals place travelers within a quick drive of an abundance of quintessential experiences. Within a 10-minute jaunt of many rentals, vacationers can soak up the stunning scenery of Connecticut's unspoiled river valley aboard the historic Essex Steam Train. From the same location, those who are longing to be out on the water can head off on an evening riverboat cruise. Travelers exploring without kids in tow will want to include a visit to nearby Bishop's Orchard Farm Market & Winery on their Westbrook travel list.


Indoor and outdoor delights in Westbrook

Souvenir hunters and fashionistas find that an array of unique stores and a well-stocked mall means a helping of retail therapy is always an option, and if you're in need of a little downtime after choosing your new must-haves, everything from casual bites to full-on gourmet fare can be savored in the town's dining spots. Those who prefer to spend their time outdoors can expect to be equally impressed. Beautiful beaches strewn with shells and tidal treasures, and mile after mile of pristine coastal reserve, mean it's never been easier to squeeze in some outdoor time with family and friends.


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.

Natural features

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:

  • Crystal Lake Town Park (2 mi / 3.3 km)
  • Harvey's Beach (2.9 mi / 4.7 km)
  • Hammonasset Beach (5.6 mi / 9.1 km)
  • Hammonasset Beach State Park (5.8 mi / 9.3 km)
  • Goose Island (6.2 mi / 10 km)
  • Gillette Castle State Park (9.8 mi / 15.8 km)
How to get there

How to get to and around Westbrook

Fly into New Haven, CT (HVN-Tweed - New Haven Regional), the closest airport, located 23 mi (37 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into New London, CT (GON-Groton - New London), which is 21.1 mi (34 km) away.

What are the top vacation rentals in or near Westbrook?

The heart wants what it wants, and right now it's longing for a vacation. Now's the time to pack your bags and take off to one of these top vacation rentals in or near Westbrook:

  • Make the most of handy extras like golf and off-street parking options at "Private Beach, Wide Open Ocean Views And Fireplace". Situated around 19 miles from Westbrook, this unique property has 1 bedroom and is a hit with guests.
  • "Beautifully Furnished 5 Star Home In Historic Downtown Mystic" is another top-notch choice, offering 4 bedrooms, a living room, a nearby casino and more. It's around 25 miles from Westbrook.

For even more great options, use the search bar at the top of the page to find the perfect Westbrook vacation rental for you.

Can I find log cabins to rent in or near Westbrook?

Whether you're looking to book a log cabin for a romantic getaway or an adventure with the family, we have the perfect property for you. Lock in one of these wonderful vacation rentals in or near Westbrook and enjoy being close to nature for a while:

  • "Log Cabin Nestled In Outdoor Haven" has all you need for a relaxing vacation, including a garden and a nearby waterfront. After you've unpacked, venture out and soak up the picturesque scenery.
  • Invite your pals along or snuggle up with your love at "Cozy Log Cabin On Sleeping Giant". A kitchen and games are some of the many amenities you'll find at this getaway.

What are the top-rated vacation rentals for weekend getaways in or near Westbrook?

Forget about those chores, because weekends were made for fun. Head for one of these weekend getaways in and around Westbrook and enjoy all the amazing things to do close by:

  • Located 25 miles to the east of central Westbrook, "Downtown Mystic Waterview, Central Ac" is a favorite among adventurous types and nature buffs. Get out and discover nearby outdoor attractions, such as Shennecossett Golf Course and Eastern Point Beach. If it's activities you're interested in, try kayaking or cycling.
  • Alternatively, unpack your bags at "Charming Mystic Home In Historic District". Approximately 25 miles east of Westbrook, fun activities around here include sailing and cycling. Rather see the sights? Make a detour to Westbrook Town Beach and Hammonasset Beach.

Can I find studio apartments for rent in and around Westbrook?

Get a taste of the energy and culture of Westbrook from the comfort of your own studio apartment. Whether you'd love to relax on your own or have fun with a few buddies, we'll help you find the ideal studio apartment for rent in and around Westbrook:

  • Make "Private Beach, Wide Open Ocean Views And Fireplace" your home away from home. This top property features amenities including towels and air conditioning.
  • "Downtown Mystic Waterview, Central Ac" is another good option. Make yourself at home and enjoy the use of housekeeping services, a fridge and more.

With the moolah you save on your studio apartment, you'll be able to discover more of Westbrook. Cultural attractions like Schubert Performing Arts Center and Toyota Presents Oakdale Theatre will help you better understand the character of this destination.

Can I find short term rentals in or near Westbrook?

Short-term rentals aren't hard to find in and around Westbrook. Kick back for a night or two in an upmarket bed & breakfast, a budget apartment or a roomy home. Whatever type of property you're chasing, you'll find the perfect place with Vrbo. Here are a few of our favorites:

  • If you'd love to be close to the action, "Renovated 1 Bedroom Getaway 1 Block From Mystic River In Historic Downtown" has you covered. It's within easy reach of the heart of Westbrook and a good base to explore attractions like Palace Theatre and Quassy Amusement Park.
  • Jump out of bed, pour yourself a coffee and then begin planning what to see around "Rest, Relax, Retreat - A 3bedroom Mystic Getaway". Waterbury Green and Brass Mill Center should be on your list if you stay at this popular vacation rental.

What are the best romantic weekend getaways in or near Westbrook?

Forget about roses and chocolates. Sometimes all you need is to get away for the weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Westbrook that would make even old Cupid swoon. Here are a few that'll sweep you off your feet:

  • Put on some soothing music and chill together at "Private Beach, Wide Open Ocean Views And Fireplace". Around 19 miles from Westbrook, this property has all you need for a couple's weekend away, including a fireplace and beauty services.
  • "Beautifully Furnished 5 Star Home In Historic Downtown Mystic" is another terrific option guaranteed to woo you. It's around 25 miles from Westbrook and comes with a nearby bay and a sauna.

Are there mansions for rent in or near Westbrook?

If you're seeking somewhere to reconnect with loved ones this vacation, you're going to need somewhere spacious. These mansions for rent in or around Westbrook will easily accommodate the entire gang while doing it in serious style:

  • Approximately 16 miles to the north of Westbrook is "Historic Mansion 1841". As well as its grand design and classy interiors, you'll be impressed by its high-end amenities, such as a firepit and a restaurant dining guide.
  • With a firepit, a swimming pool and a wealth of other top-notch amenities, "Mansion By The Lake, Airline Trail And Wineries In Ground Heated Pool" will get your team's tick of approval. This opulent stay is around 25 miles to the north of Westbrook.

What are the best large group vacation rentals in or near Westbrook?

Vacation with others and have more fun. Whether you're organizing an active escape with your besties or a big family gathering, you'll have your pick of large group vacation rentals in and near Westbrook:

  • A range of amenities including a garden and a kitchen make "Charming Mystic Home In Historic District" a standout. This generous retreat has 5 bedrooms and accommodates up to 12 guests. From the center of Westbrook, it's around 25 miles away to the east.
  • "Beachfront Classic New England Home With Direct Views Of Long Island Sound" is another awesome option. It's around 4 miles to the east of Westbrook, has 5 bedrooms and accommodates up to 12 guests. A fireplace and a kitchen are just a couple of things that'll help make your stay even more memorable.

What are the best houses for rent with a pool in or near Westbrook?

Nothing spells fun like a pool does. Blow up your unicorn floatie and check out these houses in or near Westbrook that come with this added bonus:

  • Make yourself comfortable at "The Beach House", where your highest priority will be pool time. Amenities such as a kitchen and a TV help make this escape a guest favorite.
  • Spend leisurely vacation days splashing around or catching a few peaceful moments beside the water at "Sister Sands - Renovated Waterfront Boho Beach House". This property is another sought-after option and offers a kitchen, a fenced yard and more.

Curious what the weather's like in Westbrook? It has an oceanic climate, with average temperatures in summer ranging from 65 ºF to 80 ºF. If you'd like more inspiration on places to stay in this impressive destination, use the search bar at the top of the page and adjust the filters to scroll through our entire range of Westbrook vacation rentals.

What are the best large family vacation rentals in or near Westbrook?

You'll always have more fun sharing the good times with the people you care about the most. Whether you're organizing a family escape or getting away with your best friends, we'll have a large vacation rental that's right for you. Here are two of our best in and around Westbrook:

  • Sleeping up to 8 guests in 4 bedrooms, "Beautifully Furnished 5 Star Home In Historic Downtown Mystic" is the ideal place to vacation with the family. This top-rated getaway is 25 miles to the east of Westbrook and has creature comforts such as a DVD player and a nearby bay.
  • Another top choice is "Charming Mystic Home In Historic District". This property is 25 miles east of Westbrook and features towels, nearby whale-watching activities and more. With 5 bedrooms accommodating up to 12 people, don't worry about leaving anyone off your guest list.

If you're hoping to visit some family-friendly attractions in the area, you won't have far to go. Lake Compounce, Quassy Amusement Park and Beardsley Zoo promise lots of fun for both adults and kids.