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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Windham holiday homes

TV, offices

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
Windham
The price is £498
includes taxes & fees
11 Feb - 12 Feb
Modern Lakeview Escape | 3BR/2BA
Property grounds

Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
10.0 out of 10, Exceptional, (1 review)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
The price is £106
includes taxes & fees
11 Feb - 12 Feb
Manor Suite,cozy newly renovated,downtown & beach
TV, fireplace, books

1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"Good communication with host. Beautifully decorated. Well appointed kitchen and bath. Great wooded views. Quiet but close to restaurants and shopping."
United States
Lecia M.
The price is £172
includes taxes & fees
24 Feb - 25 Feb
1 Mi to Maine Street! MCM-Style Home in Brunswick
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is £278
includes taxes & fees
11 Feb - 12 Feb
Modern Getaway by the Sea
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is £247
includes taxes & fees
16 Feb - 17 Feb
Full sized home
3 bedrooms, desk, iron/ironing board, travel cot

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Old Orchard Beach
10.0 out of 10, Exceptional, (6 reviews)
"I loved that the hosts live nearby and responded quickly when we needed anything. Having a washer and dryer onsite is great for longer stays. Beds were comfortable and plenty of blankets and pillows. Highly recommend this property."
United States
Terry
The price is £262
includes taxes & fees
19 Feb - 20 Feb
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Exterior

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
10.0 out of 10, Exceptional, (14 reviews)
"Our stay at this vacation home was wonderful! We had the best time relaxing and enjoying the fall weather. The property manager was responsive and helpful upon check in and check out. We will most definitely be staying there again!"
United States
Michie K.
The price is £473
includes taxes & fees
1 Mar - 2 Mar
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Microwave, oven, stovetop, dishwasher

The Barnhouse with hot tub

The Barnhouse with hot tub
New Gloucester
9.8 out of 10, Exceptional, (6 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 £222
includes taxes & fees
17 Feb - 18 Feb
The Barnhouse with hot tub
Interior

Spacious Country Home Freeport, Only 5 min to LL Bean!

Spacious Country Home Freeport, Only 5 min to LL Bean!
Freeport
9.8 out of 10, Exceptional, (16 reviews)
"It was a very relaxing house to stay in. Everything was provided in the kitchen, bathroom and bedrooms. Lots of room for all of us to mingle. "
United States
Carla S.
The price is £319
includes taxes & fees
11 Feb - 12 Feb
Spacious Country Home Freeport, Only 5 min to LL Bean!
Beach nearby, sun-loungers, beach towels

Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean
Old Orchard Beach
10.0 out of 10, Exceptional, (56 reviews)
"House was very nice, plenty of room, and accommodating."
United States
Joey S.
The price is £349
includes taxes & fees
16 Feb - 17 Feb
Beach House ∆ Prime Location ∆ Steps to the Ocean
Interior

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (25 reviews)
"Great host communication, arrival and access were easy, house was very clean and comfortable. Will definitely stay again and recommend to fellow Bowdoin families. House is in a great family neighborhood- enjoyed seeing how creative neighbors were with Halloween- would be a great place for kids! Close to town, Bowdoin and so much midcoast has to offer and explore! Thank you!"
United States
Alison O.
The price is £281
includes taxes & fees
23 Feb - 24 Feb
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
1 bedroom, Internet, bed sheets

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is £207
includes taxes & fees
16 Feb - 17 Feb
Charming 1-bedroom ADU in wonderful Portland neighborhood
Outdoor dining

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, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is £243
includes taxes & fees
11 Feb - 12 Feb
Modern & Sunny House Steps from the Promenade. Private Parking!
Property grounds

Modern Cottage with Peeks of Ocean Views

Modern Cottage with Peeks of Ocean Views
Cape Elizabeth
10.0 out of 10, Exceptional, (1 review)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
The price is £324
includes taxes & fees
16 Feb - 17 Feb
Modern Cottage with Peeks of Ocean Views
Interior

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Bridgton
10.0 out of 10, Exceptional, (58 reviews)
"Lovely getaway!"
United States
Victor R.
The price is £250
includes taxes & fees
3 Mar - 4 Mar
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway
Exterior

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
8.8 out of 10, Excellent, (3 reviews)
"Great location"
United States
Mark J.
The price is £253
includes taxes & fees
11 Feb - 12 Feb
The 87th Townhome - Local Landmark
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is £388
includes taxes & fees
11 Feb - 12 Feb
Willard Square Family Home
Beach towels

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland

Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
Biddeford
10.0 out of 10, Exceptional, (9 reviews)
"We have stayed three times and will be back"
United States
Michael W.
The price is £454
includes taxes & fees
11 Feb - 12 Feb
Spacious Home Close to Beaches! 3BR, Dog & Family Friendly, 30 Mins to Portland
Interior

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, (58 reviews)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is £218
includes taxes & fees
11 Feb - 12 Feb
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Living area

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

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
South Portland
10.0 out of 10, Exceptional, (1 review)
"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 £500
includes taxes & fees
8 Mar - 9 Mar
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.
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Top Windham Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"The front desk and valet are always amazing."
Angel 1-night trip
Posted 1 day ago
Portland Regency Hotel & Spa

Find out more about Windham

Windham Holiday Homes information

Number of reviews
344
Accommodation
868 Holiday Homes
Lowest Price
£106
Highest Price
£500