Holiday Rentals in Westbrook

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Holiday Rentals in Westbrook

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
The price is €492
includes taxes & fees
17 Feb - 18 Feb
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!

Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

10.0 out of 10, Exceptional, (55)
"Lovely, spacious and clean. We spent our Christmas holiday together with our family and the house was spacious and spotless. We had 5 adults with 2 small children in house. We hosted Christmas dinner for us and local family. Great space. Would love to rent in summer months to utilize outdoor space"
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (5)
"Loved how tranquil this site is. Was great to disconnect in nature. "
The price is €99
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Machimoodus

Historical New England coastal holiday home-2 min. from Ocean Beach

10.0 out of 10, Exceptional, (33)
"The host was incredibly kind and accommodating. We particularly enjoyed the beach pass, as we drove ~3 min to the beautiful water in the morning. The amenities were absolutely gorgeous and beyond functional. Plenty of bathrooms, showers, sinks, sitting areas, etc. for our party. We had a wonderful stay!"
Historical New England coastal holiday home-2 min. from Ocean Beach

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

10.0 out of 10, Exceptional, (23)
"I wanted to surprise my husband with a weekend get-away for him and five of his buds. The house perfectly fit those needs. Plenty of beds and space. Room for them to break out the Board Games hang and Mary was a wonderful partner in answering my questions and dealing with the "surprise" aspect of the weekend. It also turns out that the location was perfect with plenty of town for them to see if they felt like getting out of the house. 2 hours from NJ and Boston made it a nice mid-point for my...
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
adorable ranch in beach community

COZY Maple Tree Cabin - Romantic or family getaway. Private - Warm and Cozy!

10.0 out of 10, Exceptional, (26)
"We were in awe of how cool this cabin is, everyone kept saying, “ It’s like a Hallmark Christmas movie”. It couldn’t have been more perfect for our family. The 8yr old twin boys loved the air hockey table and it was great having that space upstairs for them to enjoy movies and games too. We had a great Christmas dinner and had all the amenities, perfect amount of seating. We tried s’mores at the fire pit, but made them quickly and ran in because it was 15 but we still got in another great...
The price is €726
includes taxes & fees
24 Feb - 25 Feb
COZY Maple Tree Cabin - Romantic or family getaway. Private - Warm and Cozy!

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (25)
"Meetings with friends who were staying at Mohegan Sun which was 20 minutes away. Pretty views, comfortable property. Would definitely return "
Private Guest House w/ Deck + Spectacular Views!

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

10.0 out of 10, Exceptional, (10)
"This may very well be the nicest house we have ever stayed in! It was spacious, clean and well stocked. It was so nice not to have to bring our own linens! We were pleasantly surprised with a hot tub. Thank you for a great stay!"
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
"This rental is so unique with the 2 sides, and was absolutely perfect for our wedding weekend. We had the groom’s friends staying on one side, and my friends staying on the other side. The two sides are connected through the sunroom and the backyard space is great which made bringing the whole group together so easy. The setup was also perfect for me to get ready on my own separate side the day of the wedding so that my now husband wouldn’t see me. The decor and cleanliness of the house were...
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (33)
"Lovely little cottage in a pretty, quiet neighborhood. Once you find it down the little lane, it's a great location to be in. Not far from town and close to the water, we really enjoyed relaxing at the house and in the backyard. Highly recommend."
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is €170
includes taxes & fees
17 Feb - 18 Feb
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Westbrook you may be interested in

Water's Edge Resort & Spa

3.5 star property
8.8 out of 10, Excellent, (1004)
"From the moment we arrived, we felt like family. The entire staff is remarkable and were very attentive to our special needs. It was a fantastic weekend and we look forward to returning soon!"
The price is €203
includes taxes & fees
2 Mar - 3 Mar
Water's Edge Resort & Spa

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
The price is €492
includes taxes & fees
17 Feb - 18 Feb
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (78)
"Hosts were great with easy and quick communication! House was very clean and everything is clearly labeled. "
Waterfront House with picture-perfect views from all 3 levels.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find holiday rentals in Westbrook?

Yes, there are holiday rentals close to the most popular sights in Westbrook, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Westbrook speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the spas and shopping during your trip.

What are some of the best holiday rentals that Westbrook has to offer?

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!
: This holiday home rental outside of Westbrook offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Westbrook?

Expedia has 43 holiday rentals for your stay in Westbrook.

What can I see and do in Westbrook?

Explore the area and family-friendly sights such as Essex Steam Train, or get out into nature at a spot like Westbrook Town Beach. In the wider area, you’ll find Tanger Outlets and Harvey's Beach.

What are holiday rentals like in Westbrook?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westbrook. Holiday rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.