Windham Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Windham holiday rentals

Dining

Lakefront ADU | Private Access | Projector Theater

Lakefront ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (1 review)
"A wonderful get away near a lake. Everything you need for a relxing vacation. The heated floor in the bathroom was perfect for a cold winter night. The living room was comfortable. We loved the projector screen and being able to watch Netflix on the big screen. The only improvement I would suggest, is to put a small microwave in the kitchen. All in all, a great place to stay and enjoy the Windham/Portland area! "
United States
Fred B.
The price is HK$869
HK$3,379 total
includes taxes & fees
18 Mar - 19 Mar
Lakefront ADU | Private Access | Projector Theater
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)
"Such a beautiful home and peaceful location. We loved our stay and the host was responsive and helpful with any questions we had!"
United States
Diana H.
The price is HK$1,630
HK$3,597 total
includes taxes & fees
16 Apr - 17 Apr
Mere Point Sunrise Views at Eastern Shore!
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$1,746
HK$2,901 total
includes taxes & fees
29 Mar - 30 Mar
Large, luxurious geodesic dome - 04
Interior

1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is HK$572
HK$2,111 total
includes taxes & fees
24 Mar - 25 Mar
1 Mi to Maine Street! Mcm-style Home in Brunswick
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$1,448
HK$2,475 total
includes taxes & fees
22 Mar - 23 Mar
Modern, Luxurious Cabin in the Woods - 03
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$1,585
HK$2,888 total
includes taxes & fees
18 Mar - 19 Mar
Full sized home
Beach

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (127 reviews)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is HK$845
HK$2,031 total
includes taxes & fees
18 Mar - 19 Mar
City Amenities, Casco Bay Sunrises and Natural Beauty
Smart TV

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (28 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$881
HK$1,882 total
includes taxes & fees
18 Mar - 19 Mar
Pine Point Beach private, quaint, charming studio.
Exterior detail

Clean cozy cottage 1 mile from beach.

Clean cozy cottage 1 mile from beach.
Old Orchard Beach
8.0 out of 10, Very good, (11 reviews)
"This house met all of our needs. It was updated and clean and has a nice little quiet enclosed back yard with a fire pit, grill and dining area. "
United States
Alyssa F.
The price is HK$775
HK$2,790 total
includes taxes & fees
23 Mar - 24 Mar
Clean cozy cottage 1 mile from beach.
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is HK$645
HK$1,437 total
includes taxes & fees
18 Mar - 19 Mar
Sunny Spot with Private Parking.
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7 reviews)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is HK$652
HK$1,530 total
includes taxes & fees
18 Mar - 19 Mar
Peaceful & minutes from the Old Port with private parking
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 HK$1,597
HK$3,661 total
includes taxes & fees
1 Apr - 2 Apr
3BR Coastal Gem with a 5 Min Drive to Ocean Fun
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 HK$2,349
HK$4,011 total
includes taxes & fees
18 Mar - 19 Mar
Modern Getaway by the Sea
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$4,030
HK$7,891 total
includes taxes & fees
18 Mar - 19 Mar
A historic treasure in Southern Maine, very unique and spacious
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, (68 reviews)
"Had a really nice stay. "
United States
John F.
The price is HK$5,462
HK$8,266 total
includes taxes & fees
18 Mar - 19 Mar
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
3 bedrooms, premium bedding, iron/ironing board, travel cot

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is HK$947
HK$2,935 total
includes taxes & fees
18 Mar - 19 Mar
Cozy 3BR | Pet Friendly | Near Portland | Parking
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$3,124
HK$6,818 total
includes taxes & fees
30 Mar - 31 Mar
Charming Victorian beach house 5 bedrooms. 50 steps to the beach
Property grounds

Saco/Old Orchard Beach Get Away

Saco/Old Orchard Beach Get Away
Downtown Saco
10.0 out of 10, Exceptional, (4 reviews)
"The host responded quickly and with all the info I could have ever needed. I didn't try the hot tub, but the shower in unit 2 was fantastic. All around very comfortable and clean place that i will go back to."
United States
Paul N.
The price is HK$1,221
HK$2,969 total
includes taxes & fees
18 Mar - 19 Mar
Saco/Old Orchard Beach Get Away
Desk, laptop workspace, free WiFi

HomeAwhile

HomeAwhile
4.0 star property
Scarborough
10.0 out of 10, Exceptional, (2 reviews)
"Staff fabulous, very clean"
United States
Verronika
The price is HK$744
HK$811 total
includes taxes & fees
19 Mar - 20 Mar
HomeAwhile
Dining

The Downtown Den - King Bed, Dog Friendly, Fire Pit, Parking, Family Friendly

The Downtown Den - King Bed, Dog Friendly, Fire Pit, Parking, Family Friendly
Downtown Saco
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, well appointed, clean and updated, great space! Would definitely stay again. "
United States
Lucy T.
The price is HK$1,060
HK$2,751 total
includes taxes & fees
18 Mar - 19 Mar
The Downtown Den - King Bed, Dog Friendly, Fire Pit, Parking, Family Friendly
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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

10/10 Excellent
"We stay here every time we come to Portland. Clean room, friendly staff. Shuttle is a nice bonus."
Nicole 1-night trip
Posted 2 hours ago
Clarion Hotel Portland Airport ME

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:

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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?

Luxury Lakefront Estate on 155 Acres - Pickleball, Reunions & Weddings: This holiday home rental outside of Windham is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and 1 hot tub.

How many holiday rentals are there in Windham?

Expedia has 36 holiday rentals for your stay in Windham.

What can I see and do in Windham?

Little Sebago Lake and 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 Basin 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.