Windham Vacation Rentals from $120: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Windham?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat : This vacation home rental near Windham is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Our top choices for Windham vacation rentals

A house surrounded by trees and a body of water.

1. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Windham

Michael S.

$609 nightly

Nov 20 - Nov 21

Total with taxes and fees

A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

2. Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

Westbrook

Bianca L.

$370 nightly

Nov 17 - Nov 18

Total with taxes and fees

A compact living space with a sofa, a coffee table, a TV on a stand, a floor lamp, and a bookshelf.

3. Great suburban location close to town!

Deering Center

Kaley

$68 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden cabin with a deck, outdoor seating, and a portable toilet in a forest.

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

Standish

Alex D.

$252 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

5. The Weldon Hotel

Downtown Portland

Branden

$255 nightly

Dec 1 - Dec 2

Total with taxes and fees

A narrow hallway with wooden flooring leading to a bedroom with a bed and a nightstand.

6. Portland 1-bedroom with enclosed porch & parking

Deering Center

Cricket C.

$71 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern room with a desk, chair, and large window.

7. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

South Portland

Anonymous traveler

$110 nightly

Nov 14 - Nov 15

Total with taxes and fees

A multi-story building with a stone facade, large windows, and a flat roof with dormer windows.

8. Evalina Hotel

Downtown Portland

Eric

$353 nightly

Dec 14 - Dec 15

Total with taxes and fees

A hallway with wooden beams, a hanging clothes rack, a stone-tiled floor, and a door leading to another room.

9. Cozy 1-bedroom cottage in soothing Standish with AC

Standish

Alyssa

$266 nightly

Nov 29 - Nov 30

Total with taxes and fees

A modern kitchen with a large island, bar stools, and a view through large windows.

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

North Deering

Patrick J.

$759 nightly

Nov 22 - Nov 23

Total with taxes and fees

A sandy beach with people and a play structure.

11. Sunny Spot with Private Parking

Knightville

Greg Z.

$181 nightly

Nov 15 - Nov 16

Total with taxes and fees

A porch with a green exterior, a black railing, and a chair with a cushion.

12. Three Gables Back Cove by Everrow

Rosemont

Carly B.

$432 nightly

Nov 16 - Nov 17

Total with taxes and fees

A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

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

Raymond

$243 nightly

Nov 18 - Nov 19

Total with taxes and fees

A cabin with two chairs facing a fire pit, surrounded by trees.

14. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Freeport

Kirt v.

$269 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with people, a play structure, and a view of the sea.

15. Peaceful & minutes from Old Port w/private parking

Knightville

Kelly S.

$215 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

16. Studio Apartment near downtown Walkable!

West Bayside

Rose

$121 nightly

Nov 19 - Nov 20

Total with taxes and fees

A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

17. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Munjoy Hill

Ryan B.

$192 nightly

Nov 16 - Nov 17

Total with taxes and fees

A living room with a sofa, a coffee table, a TV, and a plant.

18. Beautiful 1st Floor Apartment & Amazing Shower

Parkside

Chloe C.

$128 nightly

Nov 18 - Nov 19

Total with taxes and fees

A modern kitchen with wooden cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

19. Bright & Spacious Apartment with Amazing Shower

Parkside

Gintare V.

$126 nightly

Nov 17 - Nov 18

Total with taxes and fees

A beach with clear water, people swimming, and houses in the background.

20. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard

"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."

Gerald B.

$389 nightly

Nov 17 - Nov 18

Total with taxes and fees

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Top Windham Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent

"Friendly and welcoming staff and a wonderful room"

Clarion Pointe South Portland

10/10 Excellent

"The staff from checking in w J̌OSE, to having him bring us a hair dryer, to Vanessa bringing us a pillow, extra towels and washcloths and April for welcoming us back again as she remembered us from our last stay we're all wonderful employees.. all we're very kind and helpfull. Last trip was for medical appt and surgery and this trip was for a heart procedure and they were very well wishing.. we will ALWAYS stay at this same hotel for it FRIENDLINESS, CONVENIENCE, CLEANLINESS AND COMFORTABLY. Its our favorite hotel.. and we stay at a lot w my health.. Thank You Clarion Pointe in South Portland.."

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $120 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Things to do in Windham

Frequently asked questions

Are there vacation rentals in Windham?

Yes, we offer vacation rentals in Windham near Seacoast Adventure, or you can go with a more remote option if you're looking for extra privacy while you relax. Visitors to Windham speak positively about the lakeside and restaurants in this destination. Make sure you have time to check out the shopping and coffeehouses during your trip.

What are some of the best vacation rentals in Windham?

The Perfect Beach Escape: Cozy 4-Bedroom Retreat: This vacation home rental near Windham is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Windham?

Expedia has 37 vacation 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 Forest Lake.

What are vacation rentals like in Windham?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Windham. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a family getaway.

Windham Vacation Rentals

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Check prices for these dates

Our top choices for Windham vacation rentals

1. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

2. Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

3. Great suburban location close to town!

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

5. The Weldon Hotel

6. Portland 1-bedroom with enclosed porch & parking

7. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

8. Evalina Hotel

9. Cozy 1-bedroom cottage in soothing Standish with AC

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

11. Sunny Spot with Private Parking

12. Three Gables Back Cove by Everrow

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

14. Cabin w/ bath + kitchenette | Hot tub add-on - 03

15. Peaceful & minutes from Old Port w/private parking

16. Studio Apartment near downtown Walkable!

17. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

18. Beautiful 1st Floor Apartment & Amazing Shower

19. Bright & Spacious Apartment with Amazing Shower

20. Willard By the Sea - 30 ft to the beach- 2nd floor

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Holiday Inn Portland-By the Bay by IHG

Find out more about Windham

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