Windham Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Windham holiday rentals

Exterior detail

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, (73 reviews)
"Had a really nice stay. "
United States
John F.
The price is HK$6,522
HK$9,586 total
includes taxes & fees
5 May - 6 May
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Outdoor dining

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is HK$2,980
HK$5,256 total
includes taxes & fees
27 May - 28 May
Mere Point Sunrise Views at Eastern Shore!
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
Ligonia
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
The price is HK$2,546
HK$4,228 total
includes taxes & fees
5 May - 6 May
Modern Getaway by the Sea
2 bedrooms, WiFi, bed sheets

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (2 reviews)
"We didn’t get enough time to evaluate but from the short visit, we can say that this is the small paradise within the Main area. Best camp ground facilities we have ever seen or experienced. Looking forward to visit with friends and extended families as well. "
United States
Hrishi K.
The price is HK$2,179
HK$3,477 total
includes taxes & fees
7 May - 8 May
Large, luxurious geodesic dome - 04
Exterior

A historic treasure in Southern Maine, very unique and spacious

A historic treasure in Southern Maine, very unique and spacious
Biddeford
10.0 out of 10, Exceptional, (44 reviews)
"Loved this house. Perfect for a getting ready spot for family before a wedding. Plently of rooms and space for parking "
United States
Jeanne C.
The price is HK$4,033
HK$7,838 total
includes taxes & fees
5 May - 6 May
A historic treasure in Southern Maine, very unique and spacious
Exterior

Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck

Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Back Cove
9.8 out of 10, Exceptional, (8 reviews)
"My friends and I had a lovely time! The neighborhood is cute and easily to navigate. The beds were comfortable and the water pressure was great. All around a wonderful stay!"
United States
Sam C.
The price is HK$4,513
HK$7,481 total
includes taxes & fees
5 May - 6 May
Centrally located off Back Cove, 2nd floor 4 bedroom, 2 Bath condo w/ deck
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is HK$1,128
HK$2,186 total
includes taxes & fees
5 May - 6 May
Pine Point Beach private, quaint, charming studio.
Beach nearby

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is HK$2,801
HK$4,752 total
includes taxes & fees
1 Jun - 2 Jun
Arlie`s Digs! - One Block To Willard Beach!
Egyptian cotton sheets, premium bedding, down duvets, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is HK$3,224
HK$3,514 total
includes taxes & fees
4 Jun - 5 Jun
Fortland Island Campground
Interior

Couple's Glamping Getaway on Bonny Eagle Pond

Couple's Glamping Getaway on Bonny Eagle Pond
3.0 star property
Buxton
The price is HK$948
HK$2,783 total
includes taxes & fees
2 Jun - 3 Jun
Couple's Glamping Getaway on Bonny Eagle Pond
Outdoor dining

THE LILLIPAD.Off-grid A frame. Sebago lake region!

THE LILLIPAD.Off-grid A frame. Sebago lake region!
Standish
9.8 out of 10, Exceptional, (9 reviews)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
The price is HK$1,833
HK$2,255 total
includes taxes & fees
5 May - 6 May
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Beach nearby

Charming Victorian beach house 5 bedrooms. 50 steps to the beach

Charming Victorian beach house 5 bedrooms. 50 steps to the beach
Old Orchard Beach
9.6 out of 10, Exceptional, (18 reviews)
"We had a great time and it’s an awesome place. Can’t wait to rebook for next year. "
United States
Robert D.
The price is HK$3,910
HK$7,797 total
includes taxes & fees
1 Jun - 2 Jun
Charming Victorian beach house 5 bedrooms. 50 steps to the beach
Interior

The Gregory House in Southern Maine close to many beaches & popular destinations

The Gregory House in Southern Maine close to many beaches & popular destinations
Downtown Saco
9.6 out of 10, Exceptional, (19 reviews)
"Lots to do. Great location"
United States
Bob Z.
The price is HK$3,275
HK$6,960 total
includes taxes & fees
6 May - 7 May
The Gregory House in Southern Maine close to many beaches & popular destinations
Property grounds

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is HK$1,537
HK$2,504 total
includes taxes & fees
10 May - 11 May
Modern, Luxurious Cabin in the Woods - 03
Interior

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (15 reviews)
"We had a fantastic stay. Alexa was a wonderful host!"
United States
Desmond L.
The price is HK$3,025
HK$6,107 total
includes taxes & fees
10 May - 11 May
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
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 HK$1,371
HK$2,195 total
includes taxes & fees
10 May - 11 May
Charming 1-bedroom ADU in wonderful Portland neighborhood
Interior

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Saco
9.2 out of 10, Wonderful, (15 reviews)
"Had a great stay, very private property. House was very clean and user friendly. Would definitely stay again, thanks"
United States
Doug C.
The price is HK$2,115
HK$2,622 total
includes taxes & fees
5 May - 6 May
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Property grounds

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 HK$3,910
HK$5,508 total
includes taxes & fees
18 May - 19 May
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Exterior

Lakefront Log Home 12 feet Away from Lake

Lakefront Log Home 12 feet Away from Lake
Bridgton
10.0 out of 10, Exceptional, (64 reviews)
"great commication and amazing cabin "
United States
Matthew A.
The price is HK$3,714
HK$5,355 total
includes taxes & fees
6 May - 7 May
Lakefront Log Home 12 feet Away from Lake
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is HK$1,763
HK$3,109 total
includes taxes & fees
27 May - 28 May
Full sized home
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

HomeAwhile

HomeAwhile

8/10 Good
"The hotel was very very clean, it's new so it should be. Check in was a little different, you need to down load the OpenKey app so you can get in your room. The tub was very deep, which is greet for bath lovers. There was a HUGE TV in the sleeping area and a HUGE (65-70 IN) in the sitting area. I don't drink coffee but I noticed there was not a coffee marker in the room, no blow dryer and no iron/ironing board. The bed was a little on the firm side and the pillows were comfy. I would definitely stay there again."
Dawn 1-night trip
Posted 4 hours ago
HomeAwhile

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
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Look no further and take a look at our great range of rental properties in Windham!

Frequently asked questions

Are there holiday rentals in Windham?

Yes, there are holiday rentals in Windham close to Seacoast Adventure, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffee shops during your trip.

What are some of the best holiday rentals that Windham has to offer?

Steps from Old Port. New, Beautifully Appointed Home. Sleeps up to 11.: This holiday home rental outside of Windham is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Windham?

Expedia has 34 holiday rentals for your stay in Windham.

What can I see and do in Windham?

Sebago Lake Basin and Little Sebago Lake are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Seacoast Adventure. Other places in town to visit include Sebago Lake and Jordan Bay.

What are holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.