Windham Vacation Rentals

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Check prices for these dates

Next weekend
Mar 14 - Mar 16
In two weeks
Mar 21 - Mar 23
In one month
Apr 4 - Apr 6
In two months
May 2 - May 4

Browse Select Windham Vacation Homes

Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator
Outdoor dining

Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator

9.6 out of 10, Exceptional, (56)
"Beautiful house with lots of space. Comfortable and easy check in. Great area too"
The price is CA $866
CA $1,799 total
includes taxes & fees
Mar 5 - Mar 6
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
On the beach, sun loungers, beach towels

The Perfect Beach Escape: Cozy 4-Bedroom Retreat

10.0 out of 10, Exceptional, (95)
"We traveled to Old Orchard during February break. While OOB didn’t have a lot going on we were able to travel around Maine with an oceanfront home base. The beach was nearly empty for daily walks, plenty of sunshine to bundle up and sit on the upper deck in, and a lot of snow! We did enjoy a nor’easter while we were there. The driveway was cleared the next day and the front stairs were cleaned. We did have to do the deck out back to enjoy it. The house has everything you could need for a rental....
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
Charming 110-year former Inn 10' from the Ocean!
Property grounds

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

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!
The Moonglow! A beautiful ocean view house in Biddeford!
Terrace/patio

The Moonglow! A beautiful ocean view house in Biddeford!

9.8 out of 10, Exceptional, (100)
"located right on the beach, we stayed for February vacation which was not exactly a beach day but the view from the 2nd floor living room was perfect. Close to town and easy to get to. Would recommend. "
The Moonglow! A beautiful ocean view house in Biddeford!
Five miles from the beach, newly remodeled home with lots of privacy.
Fridge, microwave, oven, stovetop

Five miles from the beach, newly remodeled home with lots of privacy.

10.0 out of 10, Exceptional, (48)
"This is a lovely place for us to stay, it is always clean and the owners are really wonderful. It is the place for us to stay while visiting"
Five miles from the beach, newly remodeled home with lots of privacy.
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, microwave, oven, stovetop

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (75)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries
Serenity - Stunning Sebago Lake scenery
View from property

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (37)
"Beautiful property, great view of the lake, and outstanding communication with the owner. Family had a great time sitting by the fire playing cards and board games. Big snow storm made it great for sledding and tubing. I would definitely reccomend to other families looking to have a relaxing vacation. Thank you so much,The Factor Family"
Serenity - Stunning Sebago Lake scenery
East Grand Ave Fabulous Cottage
Beach

East Grand Ave Fabulous Cottage

9.2 out of 10, Wonderful, (131)
"The picture on VRBO leads you to believe you just go down the pathway shown to get to the beach when you are actually in a neighborhood and have to walk down the street to get to the beach. The house was very clean and both beds were very comfortable. The host was very fast to respond to my messages. Needs clean shower liner. We enjoyed our stay. "
East Grand Ave Fabulous Cottage
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.
Exterior

Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.

10.0 out of 10, Exceptional, (82)
"Family reunion "
Spacious Sebago Lake waterfront house with game room, hot tub, and covered deck.
Charming 4-bedroom house with Pool mins to Sebago Lake and More!
Fridge, microwave, oven, stovetop

Charming 4-bedroom house with Pool mins to Sebago Lake and More!

Charming 4-bedroom house with Pool mins to Sebago Lake and More!
Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access
Miscellaneous

Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access

10.0 out of 10, Exceptional, (21)
"We stayed here for a weekend of ice fishing, the house is as described and Peter made the process very simple. Highly recommend! "
Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access
Orchid Harbor, Bailey Island 3BR
Miscellaneous

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (1)
"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
Orchid Harbor, Bailey Island 3BR
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Exterior

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
TV

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay. The house was clean and the jacuzzi was much enjoyed. We let our vacation happy!"
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
Beautiful, Spacious Home, minutes to the Old Port!
Property grounds

Beautiful, Spacious Home, minutes to the Old Port!

10.0 out of 10, Exceptional, (1)
"We stayed for night with couples and friends. We had an amazing time and the place was so clean and exactly as described. "
The price is CA $183
CA $542 total
includes taxes & fees
Mar 9 - Mar 10
Beautiful, Spacious Home, minutes to the Old Port!
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Interior

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay with our family (including our 3yo). The home was exactly as described/photos show, and the view is simply amazing. Everything worked as expected, and the kids toys were an added bonus. Great communication with the host, would happily stay here again!"
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Fridge, microwave, oven, stovetop

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

10.0 out of 10, Exceptional, (89)
"Seadrift is a perfect place for a family get together. Spacious, comfortable, and fully equipped with every possible necessity, this beach house gave us everything we needed to enjoy a memorable five nights of total relaxation. Thank you, Patrick and Olivia"
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
5 Bedroom Lake House + HGuest House with Hot Tub!
Exterior

5 Bedroom Lake House + HGuest House with Hot Tub!

9.6 out of 10, Exceptional, (5)
"Great family and friends ice fishing getaway. Will definitely try and get there again for an ice fishing or summer vacation. Perfect size house and the hot tub a bonus. "
5 Bedroom Lake House + HGuest House with Hot Tub!
Modern, Luxury Lakefront Home on Crescent Lake, Maine

Modern, Luxury Lakefront Home on Crescent Lake, Maine

10.0 out of 10, Exceptional, (104)
"Comfortable and well equipped house. We loved the sauna and the beautiful view down by the lake."
Modern, Luxury Lakefront Home on Crescent Lake, Maine
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 property types in Windham

Lakefront House
Interior

Lakefront House

10.0 out of 10, Exceptional, (23)
"The house was clean and welcoming. The hosts were quick to respond to questions. It would be remarkable in the warm months, so you could enjoy the lake! "
The price is CA $232
CA $1,057 total
includes taxes & fees
Mar 6 - Mar 7
Lakefront House
The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (40)
"Very clean and comfortable! "
The price is CA $221
CA $241 total
includes taxes & fees
Mar 10 - Mar 11
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (101)
"We stayed to visit family in the area. The location was excellent and we loved the ocean view. Everything was very clean, except under the sofa in the living room. We searched for a dropped puzzle piece and "
Gorgeous ocean-front home with stunning beach views
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.