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

Vacation rentals in Westbrook

Browse 155 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+

  • Booking Options

    • Instant Booking

  • 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 155 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Westbrook
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped ample house

Westbrook, Middlesex County, Connecticut, United States
from $268
per night
from $268
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
from $567
per night
Outstanding(29 ratings)
from $567
per night
View deal
Cabin Westbrook
Cabin ∙ 8 guests ∙ 4 bedrooms

Cottage with BBQ & terrace | Nature view

Westbrook, Middlesex County, Connecticut, United States
from $800
per night
Outstanding(5 ratings)
from $800
per night
View deal
Cabin Westbrook
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage for 2 persons

Westbrook, Middlesex County, Connecticut, United States
from $152
per night
Outstanding(102 ratings)
from $152
per night
View deal
House Westbrook
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with yard, hot tub & BBQ

Westbrook, Middlesex County, Connecticut, United States
from $704
per night
Outstanding(28 ratings)
from $704
per night
View deal
House Westbrook
House ∙ 6 guests ∙ 4 bedrooms

House with garden, grill & private pool

Westbrook, Middlesex County, Connecticut, United States
from $651
per night
Outstanding(11 ratings)
from $651
per night
View deal
House Westbrook
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with garden, grill & patio

Westbrook, Middlesex County, Connecticut, United States
from $437
per night
Excellent(24 ratings)
from $437
per night
View deal
Cabin Westbrook
Cabin ∙ 5 guests ∙ 2 bedrooms

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

Westbrook, Middlesex County, Connecticut, United States
from $402
per night
Very good(12 ratings)
from $402
per night
View deal
House Westbrook
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with patio, grill & garden

Westbrook, Middlesex County, Connecticut, United States
from $237
per night
Outstanding(47 ratings)
from $237
per night
View deal
House Westbrook
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly beautiful house with terrace, barbeque & yard | Nature view | Dogs allowed

Westbrook, Middlesex County, Connecticut, United States
from $397
per night
Outstanding(76 ratings)
from $397
per night
View deal
Cabin Westbrook
Cabin ∙ 12 guests ∙ 4 bedrooms

Family-friendly cottage with BBQ & patio | Nature view | Pet-friendly

Westbrook, Middlesex County, Connecticut, United States
from $879
per night
Outstanding(89 ratings)
from $879
per night
View deal
Cabin Westbrook
Cabin ∙ 6 guests ∙ 3 bedrooms

Child-friendly cottage with barbeque & patio

Westbrook, Middlesex County, Connecticut, United States
from $361
per night
Outstanding(79 ratings)
from $361
per night
View deal
House Westbrook
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with terrace & BBQ

Westbrook, Middlesex County, Connecticut, United States
from $427
per night
Outstanding(155 ratings)
from $427
per night
View deal
House Westbrook
House ∙ 8 guests ∙ 3 bedrooms

House with yard, BBQ & terrace

Westbrook, Middlesex County, Connecticut, United States
from $358
per night
Outstanding(96 ratings)
from $358
per night
View deal
Cabin Westbrook
Cabin ∙ 8 guests ∙ 4 bedrooms

Cottage with pool, barbecue & hot tub | Nature view | Good for workation

Westbrook, Middlesex County, Connecticut, United States
from $242
per night
Outstanding(132 ratings)
from $242
per night
View deal

Dog-Friendly Vacation Rentals

House Westbrook
from $471
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 $357
per night
Cabin ∙ 7 guests ∙ 3 bedrooms

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

4.9
Outstanding(15 ratings)
Westbrook, Middlesex County, Connecticut, United States
Pet-friendly
View deal
Cabin Westbrook
from $344
per night
Cabin ∙ 6 guests ∙ 2 bedrooms

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

4.9
Outstanding(49 ratings)
Westbrook, Middlesex County, Connecticut, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

Apartment Westbrook
from $178
per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental apartment with 1 room for 3 persons

4.9
Outstanding(12 ratings)
Westbrook, Middlesex County, Connecticut, United States
Balcony
View deal
House Westbrook
from $839
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 $264
per night
House ∙ 8 guests ∙ 3 bedrooms

House with barbeque & terrace

5.0
Outstanding(83 ratings)
Westbrook, Middlesex County, Connecticut, United States
Balcony
View deal
See all offers

Vacation Houses With Pools

House Westbrook
from $1,094
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 $879
per night
House ∙ 12 guests ∙ 7 bedrooms

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

5.0
Outstanding(5 ratings)
Westbrook, Middlesex County, Connecticut, United States
Pool
View deal
Resort Westbrook
from $279
per night
Resort ∙ 2 guests ∙ 1 bedroom

Resort with garden, sauna & jacuzzi

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

Budget-friendly rental options

Enjoy affordable vacation rentals in Westbrook offering exceptional value for money

House Westbrook
from $349
per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, barbeque & yard | Nature view

5.0
Outstanding(61 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal
Cabin Westbrook
from $260
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Fully equipped ample cottage

5.0
Outstanding(22 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal
House Westbrook
from $209
per night
House ∙ 7 guests ∙ 2 bedrooms

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

4.9
Outstanding(135 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 $432
per night
House ∙ 6 guests ∙ 3 bedrooms

Wonderful vacation home with 3 rooms for 6 persons

5.0
Outstanding(2 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal
House Westbrook
from $427
per night
House ∙ 12 guests ∙ 5 bedrooms

Children-friendly house with grill, terrace & yard | Nature view

4.9
Outstanding(13 ratings)
Westbrook, Middlesex County, Connecticut, United States
View deal
Cabin Westbrook
from $406
per night
Cabin ∙ 8 guests ∙ 3 bedrooms

Fully equipped pleasant cottage with barbecue & yard

4.9
Outstanding(7 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 $450
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 (24)
  • Air conditioning (148)
  • WiFi (154)
  • Pool (57)
  • TV (137)
  • Kitchen (83)
  • No smoking (152)
  • Grill (98)
  • Balcony/patio (126)
  • Washing machine (71)
  • Fireplace (92)
  • Fishing (79)

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 $153
⭐ Popular amenities Pets allowed, Air conditioning and Internet
🐾 Pet friendly homes 24 homes
🏊 Vacation rentals with pools 57 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 $153 per night. Average prices for house rentals are $665 per night. Bed and breakfast rentals in Westbrook cost $338 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 57 vacation rentals available in Westbrook for renting.

Are pets allowed in vacation rentals in Westbrook?

Absolutely, there are 24 rentals in Westbrook that allow dogs , with an average nightly price of $553.

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