Vacation rentals in Westbrook - HomeToGo base64Hash Vacation rentals in Westbrook - HomeToGo

Vacation rentals in Westbrook

Browse 156 available vacation homes and compared across 8 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Services

    • Air conditioning
    • WiFi
    • Pool
    • TV
    • Kitchen
    • Balcony/patio
    • Washing machine
    • Fireplace
    • Dishwasher
    • Microwave
    • Hot tub
    • Yard
    • Crib
    • Sauna
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Westbrook

Discover your ideal Westbrook vacation rental with real-time comparisons of 156 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Westbrook
House ∙ 14 guests ∙ 6 bedrooms

House with garden, terrace & grill | Nature view | Perfect for remote work

Westbrook, Middlesex County, Connecticut, United States
This spacious house rental in Westbrook Center features a kitchen, fireplace, yard, and parking, perfect for family gatherings.
from $941
per night
Outstanding(12 ratings)
from $941
per night
View deal
Cabin Westbrook
Cabin ∙ 6 guests ∙ 4 bedrooms

Cottage with barbeque, patio & yard

Westbrook, Middlesex County, Connecticut, United States
This cozy cabin in Westbrook features a fireplace, yard, and parking, perfect for a family getaway accommodating six guests.
from $96
per night
from $96
per night
View deal
House Westbrook
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque & patio

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center offers a kitchen and parking, perfect for a group of six seeking a memorable getaway.
from $371
per night
Outstanding(58 ratings)
from $371
per night
View deal
House Westbrook
House ∙ 6 guests ∙ 3 bedrooms

House with terrace | Perfect for remote work

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center features a kitchen, parking, and space for six, perfect for your family getaway.
from $576
per night
Outstanding(21 ratings)
from $576
per night
View deal
Cabin Westbrook
Cabin ∙ 6 guests ∙ 2 bedrooms

Children-friendly charming cottage with terrace & grill | Pet-friendly

Westbrook, Middlesex County, Connecticut, United States
This cabin in Westbrook Center offers a kitchen, parking, and space for six, making it perfect for family adventures with pets.
from $359
per night
Outstanding(52 ratings)
from $359
per night
View deal
House Westbrook
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with barbecue & garden

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center offers a kitchen, yard, and parking, perfect for families or groups of up to 8.
from $618
per night
Outstanding(16 ratings)
from $618
per night
View deal
House Westbrook
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with barbeque

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center offers a kitchen, pet-friendly space, and comfort for up to four guests.
from $311
per night
Excellent(28 ratings)
from $311
per night
View deal
House Westbrook
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with BBQ & terrace

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center features a kitchen and parking, perfect for families of up to 8 seeking a memorable getaway.
from $172
per night
Outstanding(79 ratings)
from $172
per night
View deal
House Westbrook
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with terrace & BBQ

Westbrook, Middlesex County, Connecticut, United States
This waterfront house rental in Westbrook Center features a kitchen, balcony, beach access, and parking for up to six guests.
from $383
per night
Outstanding(166 ratings)
from $383
per night
View deal
House Westbrook
House ∙ 8 guests ∙ 3 bedrooms

House with yard, BBQ & terrace

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center features a kitchen, yard, and parking, perfect for families of up to eight.
from $425
per night
Outstanding(107 ratings)
from $425
per night
View deal
House Westbrook
House ∙ 8 guests ∙ 4 bedrooms

House with hot tub, terrace & barbeque | Nature view

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center offers beach access, a hot tub, and room for 8, perfect for your next getaway.
from $1,160
per night
Outstanding(29 ratings)
from $1,160
per night
View deal
House Westbrook
House ∙ 9 guests ∙ 4 bedrooms

Family-friendly vacation home with yard & barbecue | Pets allowed

Westbrook, Middlesex County, Connecticut, United States
This waterfront house in Westbrook offers beach access, a yard, a fireplace, and space for up to 9 guests, including pets.
from $672
per night
Outstanding(41 ratings)
from $672
per night
View deal
Cabin Westbrook
Cabin ∙ 6 guests ∙ 3 bedrooms

Child-friendly cottage with barbeque & patio

Westbrook, Middlesex County, Connecticut, United States
This cozy cabin in Westbrook Center features a fireplace, kitchen, and parking, perfect for family getaways of up to six.
from $387
per night
Outstanding(79 ratings)
from $387
per night
View deal
House Westbrook
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with yard, hot tub & BBQ | Nature view

Westbrook, Middlesex County, Connecticut, United States
This Westbrook house rental offers a waterfront setting with a hot tub, fireplace, and a yard, perfect for family gatherings.
from $875
per night
Outstanding(28 ratings)
from $875
per night
View deal
House Westbrook
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly house with barbecue | Water view

Westbrook, Middlesex County, Connecticut, United States
This house rental in Westbrook Center offers ocean views, beach access, and a kitchen, perfect for families of six.
from $271
per night
Outstanding(30 ratings)
from $271
per night
View deal

Vacation Houses With Pools

House Westbrook
from $1,563
per night
House ∙ 14 guests ∙ 7 bedrooms

Children-friendly wonderful house with barbeque, terrace & garden | Good for workation

5.0
Outstanding(10 ratings)
Westbrook, Middlesex County, Connecticut, United States
Pool
View deal
House Westbrook
from $596
per night
House ∙ 6 guests ∙ 2 bedrooms

Family-oriented house with hot tub, terrace & sauna

5.0
Outstanding(2 ratings)
Westbrook, Middlesex County, Connecticut, United States
Pool
View deal
House Westbrook
from $254
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden, pool & terrace | Nature view

Westbrook, Middlesex County, Connecticut, United States
Pool
View deal
See all offers

Dog-Friendly Vacation Rentals

Cabin Westbrook
from $216
per night
Cabin ∙ 7 guests ∙ 3 bedrooms

Charming cottage with patio, BBQ & garden | Pets are welcome

4.9
Outstanding(18 ratings)
Westbrook, Middlesex County, Connecticut, United States
Pet-friendly
View deal
House Westbrook
from $314
per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard, patio & grill

Westbrook, Middlesex County, Connecticut, United States
Pet-friendly
View deal
Cabin Westbrook
from $360
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Children-friendly cottage with barbecue & terrace | Good for workation | Pets allowed

4.4
Very good(12 ratings)
Westbrook, Middlesex County, Connecticut, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

House Westbrook
from $390
per night
House ∙ 8 guests ∙ 3 bedrooms

House with barbeque & terrace

5.0
Outstanding(88 ratings)
Westbrook, Middlesex County, Connecticut, United States
Balcony
View deal
House Westbrook
from $758
per night
House ∙ 10 guests ∙ 4 bedrooms

House with terrace & garden | Nature view

Westbrook, Middlesex County, Connecticut, United States
Balcony
View deal
House Westbrook
from $423
per night
House ∙ 4 guests ∙ 2 bedrooms

House with 2 rooms for 4 persons

Westbrook, Middlesex County, Connecticut, United States
Balcony
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Westbrook offering exceptional value for money

House Westbrook
from $973
per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation home with 3 rooms for 7 persons

Westbrook, Middlesex County, Connecticut, United States
View deal
House Westbrook
from $284
per night
House ∙ 7 guests ∙ 2 bedrooms

Family-oriented vacation home with grill & garden | Nature view

4.9
Outstanding(148 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal
House Westbrook
from $244
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with patio, grill & garden

4.9
Outstanding(47 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal

Top-Rated Vacation rentals in Westbrook

Book the highest-rated Westbrook vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Westbrook
from $466
per night
House ∙ 6 guests ∙ 3 bedrooms

Nice vacation home with 3 rooms for 6 persons

5.0
Outstanding(2 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal
Bed and breakfast Westbrook
from $226
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with patio & yard

4.9
Outstanding(150 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal
Bed and breakfast Westbrook
from $305
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with patio & garden | Garden view

4.9
Outstanding(150 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Westbrook

How are reviews collected?
Ilene T.
Guest verified by HomeToGo

The home was wonderful. The view was phenom! Every convenience we could have asked for was provided. The owner was absolutely gracious and prompt in response to queries. The neighborhood was quiet and we could walk without any concerns. There was a clean, private beach available for the neighborhood. Nothing was a far drive and there was so much to do. Just fantastic!

Reviewed on 10/6/2025 | Couple
House Westbrook
from $301
per night
House ∙ 6 guests ∙ 3 bedrooms
4.5
Excellent(2 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal

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Popular Features & Amenities in Westbrook

  • Pet-friendly (23)
  • Air conditioning (149)
  • WiFi (153)
  • Pool (56)
  • TV (137)
  • Kitchen (84)
  • No smoking (151)
  • Grill (99)
  • Balcony/patio (127)
  • Washing machine (68)
  • Fireplace (91)
  • Fishing (80)

Finding a property with a pool shouldn't be too difficult in Westbrook. One-third of the rentals provide pools. Interestingly, our data shows that more hotel room have a pool than condo. In addition, they can host 6 vacationers, on average, while condo with pools can accommodate an average of 6 vacationers. You can also compare and find a rental with a pool near the water, which is the case for nearly all of the rentals in this destination.

Explore the New England seafront with a vacation homes in Westbrook

Along the banks of the Long Island Sound, Westbrook is a serene coastal town. Here you can relax in a waterfront cottage, unwind in a cozy bed and breakfast or an upscale resort and spa with views of the Sound.

Where are the unique attractions in Westbrook?

Outlets, fitness and nature walks

With a wide range of high-end stores, Tanger Outlets is the ideal destination for bargain-hunters. The picturesque grounds of the shopping center feature benches for relaxing on your shopping marathon, and even a life-size railroad locomotive.

Fitness on the Water is a fun-filled exercise spot for people of all ages. It offers an incredible waterfront view while you exercise. The fitness center provides many different types of classes and events.

The Stewert B. McKinney National Wildlife Refuge is a coastal reserve with well-maintained paths along the coast of Connecticut. These coastal wetlands are home to a variety of wildlife and birds.

Information about vacation rentals in Westbrook

🏡 Vacation rentals available 156 rentals
🌙 Nightly prices starting at $95
⭐ Popular amenities Pets allowed, Air conditioning and Internet
🐾 Pet friendly homes 21 homes
🏊 Vacation rentals with pools 58 homes
4 reviews
Westbrook vacation rentals have an average rating of 4.5/5 on 4 reviews left by travelers.

Frequently Asked Questions

What is the typical nightly price for a vacation home in Westbrook?

On average, vacation rentals in Westbrook cost around $95 per night. Average prices for house rentals are $752 per night. Bed and breakfast rentals in Westbrook cost $339 per night on average.

How many vacation homes are available to book in Westbrook?

There are 156 vacation homes in Westbrook to browse and book for your next trip.

What are the most popular amenities for vacation homes in Westbrook?

If you're looking to book a vacation rental in Westbrook, travelers search for vacation homes with these amenities: Air conditioning, Pets allowed and Internet.

How many vacation homes with pools are in Westbrook?

Browse 58 vacation rentals available in Westbrook for renting.

Are pets allowed in vacation rentals in Westbrook?

Absolutely, there are 21 rentals in Westbrook that allow dogs , with an average nightly price of $605.

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