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Holiday Homes in Westbrook

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Westbrook holiday homes

A window with a view of a snowy landscape and bare trees.

1. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$575
includes taxes & fees
5 Oct - 6 Oct
Tranquility between the Lakes & Sea
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
The price is NZ$1,652
includes taxes & fees
6 Oct - 7 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A dirt path in a park with autumn foliage.

3. 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 NZ$1,092
includes taxes & fees
7 Oct - 8 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

4. 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 NZ$682
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

5. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (14 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is NZ$1,521
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A two-story house with a balcony, a covered patio, and a fenced yard.

6. 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, (109 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is NZ$1,167
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries
A beach with footprints, a person standing, and birds on the sand.

7. 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
8.0 out of 10, Very good, (2 reviews)
"Place was clean and cozy. Big yard for games and a fire pit for s’mores. Based on previous review I brought pots/pans but didn’t need them. Everything was available. Stove is gas and I was not familiar with using one so that was the only “challenge”We had a ball and the place was perfect for us!!"
United States
Anonymous traveller
The price is NZ$590
includes taxes & fees
6 Oct - 7 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

8. Gorgeous 3-bedroom house in charming Portland

Gorgeous 3-bedroom house in charming Portland
North Deering
9.0 out of 10, Wonderful, (4 reviews)
"This place was exactly as it looks in the photos. Really conveniently located with good amenities."
United States
Bridget M.
The price is NZ$1,313
includes taxes & fees
31 Oct - 1 Nov
Gorgeous 3-bedroom house in charming Portland
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

9. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (82 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is NZ$1,983
includes taxes & fees
5 Oct - 6 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A building named Willard Square with a storefront and a red vehicle parked outside.

10. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
Willard Square Family Home
A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

11. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.4 out of 10, Exceptional, (3 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 NZ$1,385
includes taxes & fees
28 Oct - 29 Oct
Windham Lakefront: Fire Pit and Modern Comforts
Kitchen and center island

12. Upscale Spacious OOB Beach House - Seasonal Heated Pool

Upscale Spacious OOB Beach House - Seasonal Heated Pool
Old Orchard Beach
10.0 out of 10, Exceptional, (19 reviews)
"There is plenty of space to sleep within the home. Having the pool in the back yard was awesome, we tended to use the pool more than going to the beach because it was fogged in."
United States
Karen R.
Upscale Spacious OOB Beach House - Seasonal Heated Pool
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

13. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$881
includes taxes & fees
1 Nov - 2 Nov
Modern & Sunny House Steps from the Promenade.
A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

14. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
United States
Maris P.
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

15. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is NZ$676
includes taxes & fees
11 Oct - 12 Oct
Quiet Spot in lovely Freeport neighborhood
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

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.
Spacious Portland Home + Parking
A two-story brick building with a front porch, a black door, and a window with a white frame.

17. 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 NZ$1,060
includes taxes & fees
2 Nov - 3 Nov
The 87th Townhome - Local Landmark
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

18. 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 NZ$496
includes taxes & fees
5 Oct - 6 Oct
Cozy 2-bedroom house with shared beach access to Sebago Lake
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

19. Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (20 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is NZ$1,595
includes taxes & fees
28 Oct - 29 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.
A modern kitchen with a bar area, wooden ceiling, and skylights.

20. The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (10 reviews)
"This was the perfect spot for my friends and I who were attending a wedding down the road! Great location, lovely property and very clear instructions from the hosts! "
United States
Jen V.
The price is NZ$619
includes taxes & fees
14 Oct - 15 Oct
The Barnhouse with hot tub
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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Top Westbrook Hotel Reviews

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

10/10 Excellent
"Clean, friendly staff"
Carlos 1-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Westbrook

Westbrook Holiday Homes information

Number of reviews
342
Accommodation
857 Holiday Homes
Lowest Price
NZ$496
Highest Price
NZ$1,983