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Holiday Homes in Westbrook

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Featured Holiday Homes in Westbrook

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (50)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Summer Fun, Lake View, Firepit, Outdoor grilling, walk to the lake

8.0 out of 10, Very good, (9)
"Perfect location and communication with the property manager"
Summer Fun, Lake View, Firepit, Outdoor grilling, walk to the lake

Maine Cottage

9.8 out of 10, Exceptional, (82)
"We loved everything about our stay! "
Maine Cottage

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (53)
"This apartment was very clean, modern, and fairly private, located on a quite street, but still close enough to walk to shops, cafes, breweries. Only about half a mile from downtown. Would definitely stay again!"
Sunny Modern Oasis in Portland’s Trendy East End

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (43)
"Nice house , nice host , everything was great!"
Serenity - Stunning Sebago Lake scenery

Beachfront, Just steps and you're on the beach!

10.0 out of 10, Exceptional, (1)
"We loved our stay at the cottage. It was exceptionally clean and quiet. "
Beachfront, Just steps and you're on the beach!

Elegant and efficient Island home 4 miles from downtown Portland

Elegant and efficient Island home 4 miles from downtown Portland

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Quaint Cottage Vacation

9.0 out of 10, Wonderful, (27)
"Had a great time!!"
Quaint Cottage Vacation

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (127)
"We loved our stay here. Everything was clean. My kids loved the toy blocks and running out on the beach. There is a playground nearby on the beach. Views are amazing and the area is very quiet. Great vacation!"
Charming 110-year former Inn 10' from the Ocean!

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.4 out of 10, Very good, (53)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Luxurious Penthouse with Modern Design in Downtown

9.8 out of 10, Exceptional, (12)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown

Spacious Lakehouse +Private Dock+Firepit+Kayaks

10.0 out of 10, Exceptional, (1)
"Perfect Lakefront Getaway on Panther PondWe had a fantastic week at this beautiful lake house on Panther Pond. The home was clean, spacious, and had a great kitchen.The lake was peaceful and perfect for swimming and kayaking. We spent most days on the water and evenings grilling and relaxing by the fire pit. One enjoyable perk was the ping pong table in the basement — we had nightly tournaments that kept us entertained.The location was quiet yet close to stores and towns like Raymond and...
Spacious Lakehouse +Private Dock+Firepit+Kayaks

Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home

10.0 out of 10, Exceptional, (1)
"Wonderful place to stay provided so many amenities. Beautiful views of Curtis Bay. Would definitely come back! "
Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home

Spacious 5BR Family Dream with Private Beach Access

10.0 out of 10, Exceptional, (1)
"Great property! Spacious and comfortable.Nice location."
Spacious 5BR Family Dream with Private Beach Access

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

9.6 out of 10, Exceptional, (65)
"We thoroughly enjoyed our stay at the Portland Cottage! It was a wonderful location, extremely clean, and incredible cozy. Paul is a delightful host!"
New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
8.8 out of 10, Excellent, (6)
The price is AU$3,404
includes taxes & fees
17 Aug - 18 Aug
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Luxury 5BR/5 ensuite baths • Oceanfront retreat directly on the beach !

Luxury 5BR/5 ensuite baths • Oceanfront retreat directly on the beach !

Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!

10.0 out of 10, Exceptional, (61)
"Great stay!"
Tranquil, serene Sebago Lakefront House on 2 wooded acres - 300ft waterfront!
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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