Windham, ME Vacation Homes from SAR 937

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

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Our top choices for Windham vacation homes

A two-story house with a green exterior and red trim, surrounded by trees with autumn leaves.

1. Serenity between the lakes and seashore

Westbrook

richard a.

SAR 1,080 total

includes taxes & fees

31 Oct - 1 Nov

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

2. Tranquility between the Lakes & Sea

Westbrook

Bernie G.

SAR 1,224 total

includes taxes & fees

30 Oct - 31 Oct

A dirt path in a park with autumn foliage.

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

Westbrook

Genevieve W.

SAR 2,361 total

includes taxes & fees

30 Oct - 31 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.

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

Westbrook

damean s.

SAR 3,841 total

includes taxes & fees

31 Oct - 1 Nov

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

5. Gorgeous 3-bedroom house in charming Portland

North Deering

Bridget M.

SAR 2,552 total

includes taxes & fees

31 Oct - 1 Nov

A covered wooden deck with a view of a building's exterior.

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

Buxton

Hope T.

SAR 1,281 total

includes taxes & fees

30 Oct - 31 Oct

A modern kitchen with a dining area, a living room with a sofa, and a large window.

7. Cozy Family Home w/ Beach Access

Raymond

glen l.

SAR 1,734 total

includes taxes & fees

1 Nov - 2 Nov

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

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

Raymond

SAR 1,039 total

includes taxes & fees

18 Nov - 19 Nov

A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

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

East Deering

Mike G.

SAR 4,175 total

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

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

Yarmouth

Michelle T.

SAR 3,072 total

includes taxes & fees

1 Nov - 2 Nov

A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

11. Family, friends, Gathering

Standish

Logan R.

SAR 6,170 total

includes taxes & fees

5 Nov - 6 Nov

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

West End

Susan d.

SAR 1,368 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a central island, black chairs, and pendant lighting.

13. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

SAR 1,894 total

includes taxes & fees

1 Nov - 2 Nov

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

14. Quiet Spot in lovely Freeport neighborhood

Freeport

SAR 1,514 total

includes taxes & fees

2 Nov - 3 Nov

A living room with a sofa, armchair, and coffee table, a kitchen with appliances, and a dining area with chairs.

15. Newly Remodeled Cottage with AC- Sebago Lake Area

Raymond

SAR 1,915 total

includes taxes & fees

8 Nov - 9 Nov

A light blue door with a numerical address sign, a doormat, and two wall-mounted lights.

16. Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

Biddeford

"This little house was absolutely charming! The owners were very accommodating and flexible with our dates and last minute booking. The house is incredibly cozy and the outdoor porch was a big hit. The location of this house is also amazing as you have access to the ocean, marsh and a beautiful pond. E would love to return with our grandkids who would love it! Thank you Shannon and Jim for sharing your special house with us!"

Allison B.

SAR 937 total

includes taxes & fees

31 Oct - 1 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.

17. 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.

SAR 1,571 total

includes taxes & fees

11 Nov - 12 Nov

A wooden covered porch with a green door, potted plants, and a red watering can.

18. Charming West End Victorian

Parkside

SAR 2,910 total

includes taxes & fees

30 Oct - 31 Oct

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

19. Willard Square Family Home

Willard Beach

David W.

SAR 2,542 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with a wooden dining table, a ceiling fan, and a view of the outdoors.

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

Casco

Edward R.

SAR 1,133 total

includes taxes & fees

28 Nov - 29 Nov

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Top Windham Hotel Reviews

Portland Regency Hotel & Spa

10/10 Excellent

"I chose to take a day and night for me. Booked day of.. based on proximity, price (via Hotels.com), and did I get a good “vibe”. I do not regret my descision one but smiling walking in Monday. Walked out Tuesday, after a pit stop at the spa (incredible massage), with an even bigger smile. I scheduled a follow up massage the next day for the next Tuesday. Now, do I stay again this Monday? 🤔"

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

10/10 Excellent

"This is a great option for crashing after a late flight into PWM. The shuttle came right away after I got it and called, super clean and spacious room and nice breakfast bar in the morning. Would definitely go back!"

Ramada Plaza by Wyndham Portland

8/10 Good

"I was there for 2 nights and was told when I checked in housekeeping would not be cleaning my room but if I needed anything just ask. I was fine with that. Room was clean, bed was comfortable, and there was a fridge in the room. The shower head was adjustable for different water flows but the pressure made them all seem about the same. The shower covering over the old tub felt weird as there was some give to the floor as you moved around in the shower. The bathroom was clean and they provided facecloths as well as towels. There was a sink in the bathroom as well as one outside the bathroom door. Room had a balcony. I would definitely stay hear again for the combination location, affordability, cleanliness and friendliness of staff."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham vacation homes

1. Serenity between the lakes and seashore

2. Tranquility between the Lakes & Sea

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

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

5. Gorgeous 3-bedroom house in charming Portland

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

7. Cozy Family Home w/ Beach Access

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

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

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

11. Family, friends, Gathering

12. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

13. Modern & Sunny House Steps from the Promenade.

14. Quiet Spot in lovely Freeport neighborhood

15. Newly Remodeled Cottage with AC- Sebago Lake Area

16. Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

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

18. Charming West End Victorian

19. Willard Square Family Home

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

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Portland Regency Hotel & Spa

Portland Harbor Hotel

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

Cambria Hotel Portland Downtown-Old Port

Inn at St John Portland In-Town

Motel 6 Portland, ME

Ramada Plaza by Wyndham Portland

Search Vacation Homes in Windham

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham vacation homes

1. Serenity between the lakes and seashore

2. Tranquility between the Lakes & Sea

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

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

5. Gorgeous 3-bedroom house in charming Portland

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

7. Cozy Family Home w/ Beach Access

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

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

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

11. Family, friends, Gathering

12. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

13. Modern & Sunny House Steps from the Promenade.

14. Quiet Spot in lovely Freeport neighborhood

15. Newly Remodeled Cottage with AC- Sebago Lake Area

16. Fabulous 3-bedroom house in Biddeford perfect for your beach getaway

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

18. Charming West End Victorian

19. Willard Square Family Home

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

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Portland Regency Hotel & Spa