
Vacation rentals in Westbrook
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Quick stats about vacation rentals in Westbrook

Total vacation rentals
Explore 160 vacation rentals in Westbrook

Nightly prices starting at
Westbrook vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

Verified guest reviews
Over 4,740 verified reviews to help you choose

Family-friendly vacation rentals
120 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
160 of Westbrook vacation rentals include wi-fi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Westbrook rentals

4.8 Average rating
Westbrook stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated vacation rentals in Westbrook
Guests agree: these stays are highly rated for location, cleanliness, and more.

Adorable single story cottage-by-the-sea
Adorable, quiet seasonal single story cottage-by-the-sea, in Westbrook, CT. The cottage is located approximately 25 yards from private West Beach. You will love the large front porch and living room with plenty of space for everyone. Updated kitchen with all the amenities. Two bedrooms with closets & drawers. Picnic bench with stainless steel grille & Bonfire Solo Stove outside. Hot & cold outdoor shower to wash off the sand, after a day at the beach. Off road parking on the side of the house.

Remodeled cozy home near beach
.4 mile walk to Beach/Westbrook Elks Club, this newly remodeled home is perfect for a couple looking to relax and enjoy what the CT Shoreline has to offer. Close to restaurants and shopping, this house boasts a spacious queen bedroom, walk in shower, large kitchen, living room, dining room, sitting area, 2 gas fireplaces, & laundry room. Enjoy the private outdoor deck with dining table, Adirondack chairs, porch swing and hot tub. Cook outside on the Weber grill or take a ride on bikes provided.

Peaceful Riverfront Cottage w/Dock, Walk to Beach
This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Adorable Cottage, 5 min walk to water & coffee
Experience the quaint charm of our Westbrook, CT, with this adorable coastal retreat just a 3 minute walk to middle beach. Ideal for traveling workers, couples, or small families, this 2-bedroom, 1-bath unit was recently renovated with light, bright touches! Guests can also enjoy an outdoor fire pit and grill. Included is a TV for entertainment, free internet for remote work and driveway parking for convenience. Consider renting our other unit for larger families at this sweet beach community.

The Dragon Fly Garden
The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Steps to Beach! *Cozy Cottage* Pet Friendly
Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

A Beach House Gem
Beautiful beach cottage with a private beach. Sleeps up to 6 comfortably with two full beds and 1 queen in the master. with a beautiful balcony Full bath upstairs,1/2 off the kitchen entrance outside key on the key chain The main living area has a TV, air conditioning, and sliding doors to a deck. The updated kitchen has a dishwasher, microwave, cooktop, oven, and coffee maker. There are 2 parking spots in front of the garage The house is not winterized there are no bookings from Nov1

Money Point Beach House- Deck+Views + Beach Access
Available all year round, heated beach house! Keep it simple at this peaceful home. Access to small private beach. Large fenced in backyard. Enjoy the large wraparound deck and views of Long Island sound and wetlands and a nature preserve behind the house. People ask why the area is “Money Point.” According to local historians, our small beach area is rumored to be a depository for Captain Kidd’s gold. Short ride to the Waters Edge resort (we host many wedding guests).

Sea Salt Air Changes Everything
Sea Salt Air Changes Everything... The mood. The conversation. The momentum. When you are here you will find yourself at the crossroads of nature and civilization. Stroll to a private association beach from this restful retreat. Stretch out on the deck overlooking swaying seagrass. Sing in the outdoor shower. Go on, no one is listening. Tasteful appointments. Elegance abounds. Salt life refined with the comforts that nourish your soul. Solitude awaits you.

Waterfront Bliss Tiny Home
Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Cozy Loft Getaway
Our private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

Adorable Beach House on LI Sound
Beach House with incredible views of the Thimble Islands - 4 min walk to Restaurants including Lenny’s, Zagat award winner for fresh local seafood - 1 min walk to Bud’s Fish Market - 3 min walk to Indian Neck Liquor - 3 min drive to brewery w/ food trucks & music - 4 min drive to Branford Green w/ specialty stores, coffee & ice cream
Popular amenities for Westbrook vacation rentals
Other great vacation rentals in Westbrook

Secret Seaside Stone Cottage

Zion's Light Beach Cottage

Home Away From Home

Red Bird Waterfront Home. Dock available extra!

The Connecticut Cottage | Historic Modern Charm

Cozy Beach Home Mid NYC-Bos/Comfy Getaway all year

King Suite, Easy walk to Beach

Shoreline postmodern apartment
When is the best time to visit Westbrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 918 | ﺩ.ﺇ 933 | ﺩ.ﺇ 914 | ﺩ.ﺇ 918 | ﺩ.ﺇ 1,028 | ﺩ.ﺇ 1,043 | ﺩ.ﺇ 1,172 | ﺩ.ﺇ 1,285 | ﺩ.ﺇ 1,120 | ﺩ.ﺇ 1,010 | ﺩ.ﺇ 1,010 | ﺩ.ﺇ 1,025 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
What are the best places to stay in Westbrook?
Vacation rentals near the waterfront, cozy cottages, and locally owned inns in quieter neighborhoods are frequently suggested places to stay. Many options provide easy access to both beaches and shops.
What are the best things to do in Westbrook with kids?
Families can enjoy building sandcastles at Westbrook’s beaches, exploring community playgrounds, or boating near local marinas. Nature preserves with easy trails are frequently suggested for low-key outdoor adventures.
What are some of the best things to do in Westbrook?
You can explore sandy beaches, visit local marinas, or browse unique shops around town. Westbrook has art galleries and nature preserves that are often recommended for a relaxing outing.
How is the weather in Westbrook?
Westbrook has cold, snowy winters between 24–38°F (–4–4°C) and warm summers with highs near 82°F (28°C). Spring and fall bring mild temperatures and occasional rain, so layers and a light rain jacket are useful.
When is the best time to visit Westbrook?
Late spring through early fall is often recommended for milder weather and outdoor activities, with many visitors enjoying the beaches and nature trails during these seasons. Cooler months are quieter and appeal to those seeking a peaceful getaway.
What are the best places to visit in Westbrook?
The town beach, marinas, and nature preserves are among the most popular places to visit in Westbrook. Art galleries and quaint shops add local character, especially around the town center.
What are some hiking trails in Westbrook?
You can explore easy walking paths in local nature preserves and coastal marshes around Westbrook. Trails often feature viewpoints, boardwalks, and opportunities to spot native wildlife.
What are some family activities we can do in Westbrook?
Families often explore the beaches, visit marinas for boat watching, or participate in arts and crafts events around the community. Nature preserves and local playgrounds are also welcoming spots for all ages.
What are some of the best day trip ideas from Westbrook?
You can explore neighboring coastal towns, visit local vineyards, or stroll through historic villages around the region. Wildlife refuges, state parks, and maritime museums are also popular choices for a varied outing.
Are there any pet friendly accommodations available in Westbrook?
Many vacation rentals and some local inns in Westbrook welcome pets, especially near the beach or quieter neighborhoods. Always confirm policies for pets before booking your stay.
What are some local tips for visiting Westbrook?
Locals often suggest bringing layers for changing weather and exploring markets for fresh seafood. Early mornings at the beach or nature reserves tend to be quieter, and many small shops have a relaxed, welcoming pace.
What is Westbrook known for?
Westbrook is known for its sandy beaches, vibrant marinas, and a tradition of fresh seafood. The town has scenic nature preserves and a welcoming small-town atmosphere that draws visitors seeking coastal charm.
What are the best hidden gems to explore in Westbrook?
Tucked-away art studios, small nature trails, and locally run ice cream shops invite a more personal look at Westbrook. Visiting local markets or lesser-known beaches can reveal a quieter side of this coastal town.
What are the best foods to try in Westbrook?
Westbrook has seafood-focused menus featuring dishes like lobster rolls, clam chowder, and fried oysters. Locally made ice cream and New England–style pizza are also frequently suggested treats.
What should I bring for a trip to Westbrook?
Pack casual clothes, layers for cooler evenings, and a light jacket, especially in spring or fall. Comfortable shoes, sunscreen, and rain gear can help you enjoy both beaches and nature trails around Westbrook.
What is the nightlife in Westbrook like?
Nightlife in Westbrook is relaxed, with local pubs, casual music venues, and waterfront restaurants providing a laid-back scene. Many spots feature live performances or community events, especially in warmer months.
What are the most popular events or festivals in Westbrook?
Westbrook hosts summer concerts on the green, craft fairs, and seasonal celebrations around Memorial Day and Independence Day weekends. Community festivals featuring local food and music are frequently suggested by residents.
Are there family friendly vacation rentals in Westbrook?
Westbrook has a variety of family-friendly vacation rentals, including cottages and homes with multiple bedrooms or equipped kitchens. Many options are located near beaches, parks, or quiet neighborhood settings.
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