Windham Holiday Houses | Expedia.co.nz

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

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Our top choices for Windham holiday homes

A window with a view of a snowy landscape and bare trees.

1. Tranquility between the Lakes & Sea

Westbrook

Thomas C.

includes taxes & fees

22 Oct - 23 Oct

A dirt path in a park with autumn foliage.

2. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

Westbrook

Genevieve W.

includes taxes & fees

21 Oct - 22 Oct

A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

3. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Westbrook

damean s.

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

4. Gorgeous 3-bedroom house in charming Portland

North Deering

Bridget M.

A beach with a dock, a boat, and signs indicating a private dock and no fishing from the dock.

5. Cozy Family Home w/ Beach Access

Raymond

includes taxes & fees

21 Oct - 22 Oct

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

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

Raymond

includes taxes & fees

27 Oct - 28 Oct

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

Buxton

Annette

includes taxes & fees

27 Oct - 28 Oct

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

East Deering

Mike G.

includes taxes & fees

26 Oct - 27 Oct

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

Yarmouth

Michelle T.

includes taxes & fees

21 Oct - 22 Oct

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

10. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

West End

Susan d.

includes taxes & fees

29 Oct - 30 Oct

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

11. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

23 Oct - 24 Oct

12. ANY BIG PARTY!!!!

Standish

Logan R.

includes taxes & fees

22 Oct - 23 Oct

A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

13. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

includes taxes & fees

2 Nov - 3 Nov

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.

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

Munjoy Hill

"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...

Maris P.

includes taxes & fees

11 Nov - 12 Nov

A living room with a sofa, armchairs, a coffee table, and a patterned rug.

15. Newly Remodeled Cottage with AC- Sebago Lake Area

Raymond

includes taxes & fees

21 Oct - 22 Oct

A small, single-story shed with a door and a window, surrounded by a wooden deck and a wooden fence.

16. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

Casco

Edward R.

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with white cabinets, a dining area with a table and chairs, a sofa, and a coffee table with books.

17. Fully Updated Lake View Home on Thomas Pond

Casco

A building named Willard Square with a storefront and a red vehicle parked outside.

18. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

12 Nov - 13 Nov

A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

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

Scarborough

Stuart R.

includes taxes & fees

26 Oct - 27 Oct

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

Casco

loie H.

includes taxes & fees

19 Nov - 20 Nov

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Top Windham Hotel Reviews

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

8/10 Good

"Parking on-site $10/day Comfortable room"

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good

"Clean and utilitarian. We were happy with the room and the bed was super comfy. Always love an airport shuttle... wish it would have been willing to drop us 1/2 mile away but it wasn't a difficult walk. We would definitely choose here again"

Hampton Inn Portland Downtown - Waterfront

8/10 Good

"First, the positives: location is perfect for a Portland visit. Easy walking distance to downtown and the harbor. Not far from the interstate. The staff was courteous and helpful when asked, and the property was clean and felt almost new. The negatives: for nearly mid-four figures a night there need to be more amenities. The in-room coffee was Motel 6 grade, and the breakfast as well. On our last morning, for whatever reason, the breakfast buffet, already rather skimpy, was missing many key items — no yogurt, no fresh fruit — and this not even midway through the service. As far as housekeeping goes, we stayed three nights, were away from the room most of each day, but our room was never made up. We did finally ask for some fresh towels and a resupply of tissues, and we are low-impact guests who really don’t need our bed made every day, but I was surprised that there wasn’t even an effort, or at least advance notice that we’d have to ask for housekeeping despite seeing them active in our corridors each day as we departed. I sensed that either the property was having trouble filling staff positions, or maybe they were being squeezed by their corporate overlords. In sum, for that much money I expected a little more, some extra touches that would elevate the experience beyond the basics."

Fireside Inn & Suites Portland

10/10 Excellent

"This was a great little spot- close to downtown Portland (about 15 mins). Very cozy rooms and I loved the hot tub. I want to go back in the summer to enjoy the beautiful patio (my trip was during a cold September weekend). Staff were friendly and helpful and their grab and go breakfast had tons of options."

Inn at St John Portland In-Town

10/10 Excellent

"Very classic inn vibe that was just a short drive away from the city center. Note there is no elevator for those of you with large suitcases and the stairs are a little steep and tight, but we had no issue getting our checked bag up and down from the third floor, and staff offered to help us both times. The shared bathroom was clean and the provided robes were a nice touch! Consider bringing shower shoes or flip flops to make it easier to use. Parking was easy, and if the small lot right next to the building fills up, they have a parking lot just a block away that was just as easy to use. Breakfast was also a nice touch although the area was a little tight. Expect bagels, toast, yogurt, and simpler stuff along those lines."

Find out more about Windham

Windham Holiday Homes information

Number of reviews	312
Accommodation	922 Holiday Homes
Lowest Price	NZ$485
Highest Price	NZ$2,785

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham holiday homes

1. Tranquility between the Lakes & Sea

2. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

3. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

4. Gorgeous 3-bedroom house in charming Portland

5. Cozy Family Home w/ Beach Access

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

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

8. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

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

10. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

11. Quiet Spot in lovely Freeport neighborhood

12. ANY BIG PARTY!!!!

13. Modern & Sunny House Steps from the Promenade.

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

15. Newly Remodeled Cottage with AC- Sebago Lake Area

16. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

17. Fully Updated Lake View Home on Thomas Pond

18. Willard Square Family Home

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

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

Find holiday rentals that suit your style

Top Windham Hotel Reviews

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Hampton Inn Portland Downtown - Waterfront

Fireside Inn & Suites Portland

Spark by Hilton Portland Airport Maine Mall

Holiday Inn Portland-By the Bay by IHG

Inn at St John Portland In-Town

Portland Regency Hotel & Spa

Ramada Plaza by Wyndham Portland

Find out more about Windham

Windham Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Windham

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham holiday homes

1. Tranquility between the Lakes & Sea

2. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

3. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

4. Gorgeous 3-bedroom house in charming Portland

5. Cozy Family Home w/ Beach Access

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

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

8. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

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

10. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

11. Quiet Spot in lovely Freeport neighborhood

12. ANY BIG PARTY!!!!

13. Modern & Sunny House Steps from the Promenade.

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

15. Newly Remodeled Cottage with AC- Sebago Lake Area

16. Cozy 2-bedroom Tiny Home with sauna, A/C, boat ramp access to quiet lake

17. Fully Updated Lake View Home on Thomas Pond

18. Willard Square Family Home

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

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

Find holiday rentals that suit your style

Top Windham Hotel Reviews

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Windham

Windham Holiday Homes information

Explore a world of travel with Expedia