A white church with a steeple and red accents, surrounded by autumn trees.

Search Vacation Homes in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windham vacation homes

A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

1. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for our girls trip to Portland. Private, surrounded by woods, cozy and clean! We even saw wild turkeys and deer in the yard."
United States
Jonny D.
The price is SAR 1,104
SAR 3,417 total
includes taxes & fees
25 Oct - 26 Oct
Windham Lakefront: Fire Pit and Modern Comforts
A window with a view of a snowy landscape and bare trees.

2. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is SAR 430
SAR 1,230 total
includes taxes & fees
14 Oct - 15 Oct
Tranquility between the Lakes & Sea
A dirt path in a park with autumn foliage.

3. 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 SAR 1,653
SAR 2,362 total
includes taxes & fees
12 Oct - 13 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

4. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (15 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is SAR 1,577
SAR 3,080 total
includes taxes & fees
18 Oct - 19 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

5. Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is SAR 845
SAR 1,040 total
includes taxes & fees
18 Oct - 19 Oct
Cozy 2-bedroom house with shared beach access to Sebago Lake
A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

6. Cozy Family Home w/ Beach Access

Cozy Family Home w/ Beach Access
Raymond
Cozy Family Home w/ Beach Access
A beach with footprints, a person standing, and birds on the sand.

7. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
7.4 out of 10, Good, (3 reviews)
"The property was unique, with lots of updates to the interior that met and even exceeded our needs (4 TV's!). New appliances and fully stocked with kitchen-ware. Plenty of towels and beds to indeed sleep 10 as described. The host has thought carefully about what you might need during your stay. Outdoor seating is plentiful so if the weather is good, you're all set for hanging out."
United States
Annette
The price is SAR 469
SAR 1,281 total
includes taxes & fees
20 Oct - 21 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

8. 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, (82 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is SAR 2,620
SAR 4,173 total
includes taxes & fees
12 Oct - 13 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

9. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is SAR 1,861
SAR 3,957 total
includes taxes & fees
12 Oct - 13 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
Dining

10. Family, friends, Gathering

Family, friends, Gathering
Standish
8.0 out of 10, Very good, (2 reviews)
"Beautiful property, spacious, plenty of beds and super easy to get to the lake. Owner was very responsive throughout the process."
United States
Logan R.
The price is SAR 2,704
SAR 6,173 total
includes taxes & fees
15 Oct - 16 Oct
Family, friends, Gathering
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

11. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is SAR 450
SAR 1,418 total
includes taxes & fees
12 Oct - 13 Oct
Quiet Spot in lovely Freeport neighborhood
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

12. 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, (62 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is SAR 426
SAR 1,459 total
includes taxes & fees
20 Oct - 21 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

13. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (47 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is SAR 1,127
SAR 1,920 total
includes taxes & fees
1 Nov - 2 Nov
Modern & Sunny House Steps from the Promenade.
A wooden deck with a grill area, overlooking a lake with trees in the background.

14. Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse

Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
Casco
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful setting! Wishing we could have stayed longer. Awesome communication with the host, cleanliness is impeccable. Would definitely stay here again."
United States
MaryAnn F.
Scenic 2-bedroom Tiny Home on the Lake with dock, boat ramp & screenhouse
A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

15. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
United States
Maris P.
The price is SAR 1,018
SAR 1,936 total
includes taxes & fees
11 Nov - 12 Nov
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A living room with a sofa, armchairs, a coffee table, and a patterned rug.

16. Newly Remodeled Cottage with AC- Sebago Lake Area

Newly Remodeled Cottage with AC- Sebago Lake Area
Raymond
The price is SAR 1,112
SAR 1,916 total
includes taxes & fees
13 Oct - 14 Oct
Newly Remodeled Cottage with AC- Sebago Lake Area
A building named Willard Square with a storefront and a red vehicle parked outside.

17. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is SAR 1,127
SAR 2,270 total
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A stone fireplace with a TV mounted above it, a wooden mantel, and a hanging light fixture.

18. The Outlet Studio, Rustic Comfort w Fireplace

The Outlet Studio, Rustic Comfort w Fireplace
Freeport
10.0 out of 10, Exceptional, (15 reviews)
"Cottage is just as described. Great place to stay for a few nights to explore the area.Easy walk to Outlets and Restaurants."
United States
Joanne H.
The Outlet Studio, Rustic Comfort w Fireplace
Exterior

19. Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake

Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
Casco
10.0 out of 10, Exceptional, (2 reviews)
"Clean and tidy"
United States
Edward R.
The price is SAR 920
SAR 1,134 total
includes taxes & fees
15 Oct - 16 Oct
Cozy 2-bedroom Tiny Home with hot tub, A/C, boat ramp access to quiet lake
A multi-story house with a dock and a children's play area.

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

Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
Casco
9.8 out of 10, Exceptional, (17 reviews)
"We loved the houses and esp the hot tub!"
United States
loie H.
The price is SAR 755
SAR 2,695 total
includes taxes & fees
14 Oct - 15 Oct
Exceptional Private Lakefront Retreat | Hot Tub, Sauna, Private Dock and Floats
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

8/10 Good
"Everything was clean but jacuzzi’s seemed a little dirty"
Leticia 2-night trip
Posted less than an hour ago
Ramada Plaza by Wyndham Portland