A frozen river with a bridge crossing over it, surrounded by buildings and parked cars.

Search Vacation Homes in Westbrook

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Westbrook vacation homes

1. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (29 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
The price is ¥23,053
¥54,443 total
includes taxes & fees
Sep 7 - Sep 8
Serenity between the lakes and seashore

2. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is ¥27,856
¥64,739 total
includes taxes & fees
Sep 8 - Sep 9
Tranquility between the Lakes & Sea

3. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is ¥65,637
¥158,968 total
includes taxes & fees
Sep 1 - Sep 2
Sleeps 16+ | W/D | Parking | 15 mins to Old Port

4. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is ¥64,692
¥93,548 total
includes taxes & fees
Sep 1 - Sep 2
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

5. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is ¥14,826
¥58,039 total
includes taxes & fees
Sep 3 - Sep 4
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

6. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is ¥30,577
¥115,867 total
includes taxes & fees
Sep 30 - Oct 1
Windham Lakefront: Fire Pit and Modern Comforts

7. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is ¥51,229
¥91,961 total
includes taxes & fees
Sep 15 - Sep 16
The Globe House on Munjoy Hill - Walk to Breweries

8. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
6.0 out of 10, (1 review)
"Overall, value property. It's a very old home that was slightly renovated. Pros. 3 bedrooms, washer dryer, good price Cons. Smelled musty, pans not usable for cooking, small living room.Host was great with communication, and the stay was worth the price."
United States
Renee D.
The price is ¥23,213
¥58,806 total
includes taxes & fees
Sep 28 - Sep 29
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

9. Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
9.0 out of 10, Wonderful, (2 reviews)
"The location was very convenient. Easy drive to downtown Saco and Biddeford. As well as very quick access to the highway so Portland and other points are easy to get to. Ample parking."
United States
Ellen L.
The price is ¥20,575
¥80,535 total
includes taxes & fees
Sep 1 - Sep 2
Huge New Townhome 10mins from the Beach

10. The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.4 out of 10, Exceptional, (9 reviews)
"We had a wonderful time at the property! Super close walking distance to great shopping and restaurants. Host was so responsive and even checked in to make sure we were having a great stay. Would stay again!"
United States
Amy B.
The price is ¥44,780
¥105,521 total
includes taxes & fees
Sep 1 - Sep 2
The 87th Townhome - Local Landmark

11. Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
The price is ¥48,715
¥82,590 total
includes taxes & fees
Sep 1 - Sep 2
Modern & Sunny House Steps from the Promenade. Private Parking!

12. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is ¥64,036
¥116,824 total
includes taxes & fees
Sep 1 - Sep 2
Willard Square Family Home

13. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is ¥36,020
¥44,846 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2-bedroom house with shared beach access to Sebago Lake

14. Two Beautiful apartment

Two Beautiful apartment
Back Cove
10.0 out of 10, Exceptional, (28 reviews)
"Such an amazing property and host in an incredible location! "
United States
Devin M.
The price is ¥172,753
¥244,140 total
includes taxes & fees
Sep 4 - Sep 5
Two Beautiful apartment

15. Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View
West End
9.8 out of 10, Exceptional, (14 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
The price is ¥47,387
¥98,941 total
includes taxes & fees
Sep 14 - Sep 15
Rare West End Home • Walk to Old Port, Harbor View

16. Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.6 out of 10, Excellent, (4 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is ¥48,075
¥129,705 total
includes taxes & fees
Sep 10 - Sep 11
Spacious Portland Home + Parking

17. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is ¥23,213
¥78,873 total
includes taxes & fees
Sep 1 - Sep 2
Fully Updated Airy Historic Home in South Freeport

18. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
The price is ¥21,292
¥74,336 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Family Home w/ Beach Access

19. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Oakdale
10.0 out of 10, Exceptional, (1 review)
"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "
United States
Andy W.
The price is ¥100,857
¥232,432 total
includes taxes & fees
Sep 1 - Sep 2
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

20. SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (2 reviews)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is ¥94,453
¥177,464 total
includes taxes & fees
Sep 24 - Sep 25
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Westbrook Hotel Reviews

Find out more about Westbrook

Westbrook Vacation Homes information

Number of reviews
347
Accommodation
868 Vacation Homes
Lowest Price
¥44,846
Highest Price
¥244,140