Entire home

The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks!

Photo gallery for The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks!

A spacious living room with a large window overlooking a lake, a dining area with a table and chairs, and a cozy seating area with a sofa and a coffee table. - The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! (Windham)
A dining area with a table and chairs, a potted plant, and a view of a snowy outdoor area through large windows. - The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! (Windham)
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a wooden cabinet. - The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! (Windham)
A two-story house with a stone exterior, a front porch, and a staircase leading to the entrance. - The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! (Windham)
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a bar area with a unique marble countertop. - The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! (Windham)
A firepit, laundry facilities, and a hot tub are just a few of the amenities provided at The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks!. Stay connected with free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Entire home

5 bedrooms2 bathrooms

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Add dates for prices

About this property

The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks!

  • Make your getaway to Maine one for the books with a stay at our place on Pettingill Pond in Windham.

    This charming little 3-story house is bigger than it looks, perfect for families and groups of friends alike.

    Enjoy waterfront access and beautiful views overlooking the pond from almost anywhere in the house, come relax and enjoy our home away from home any time of the year.

    HOUSE LAYOUT (funky but we love it):

    Top floor: Open-concept living area, full kitchen with an island, comfy sectional sofa, smart TV, dining area, balcony off the dining area overlooking the backyard

    Middle floor: 3 bedrooms (1 king-sized bed, 2 queen sized-beds), two full bathrooms (1 bathtub, 1 shower)

    Bottom floor: Brand new bar area and kitchenette, pull-out sofa, 4th bedroom (king-sized bed), small 5th bedroom w/ bunk beds (twin-over-double), smart TV, dart board

    OUTSIDE:

    During the summer months, we have a dock, patio furniture, a hot tub, night-glow jumbo chess, a fire pit, a grill and two kayaks available for use. Although it isn't an ideal place to swim, we hear there is great fishing in the pond!

    Dogs are always welcome.

    ***Please note, the house is located on the corner of a very busy road. There is minimal traffic noise from inside the house, but it is noticeable while outside.***

    NEARBY:

    - North Windham amenities: 5-minute drive
    - Sebago Lake - Tassel Top beach: 5-minute drive
    - Seacoast Adventure Park (mini golf, go-karting & more): 2-minute walk
    - The Deckhouse Tavern (restaurant): 2-minute walk
    - Downtown Portland: 40-minute drive

Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Kitchenette
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Shower
  • Toilet paper
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 3 pets total (up to 999 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Area rugs in public areas
  • Gravel flooring in public areas
  • Handrails in stairways
  • Smooth flooring in public areas
  • Upper floors accessible by stairs only
  • Smoking not allowed

Things to do

  • Kayak

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and lock the doors
Please place all used towels in the washing machine. Do not add detergent or run the washer, we'll take care of this!
Failure to complete these may result in a negative review from the host.

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
3 total (up to 999 lbs per pet)

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have elevators

About the neighborhood

Windham is home to this vacation home. Sebago Lake State Park and Mayberry Hill Preserve reflect the area's natural beauty and area attractions include Seacoast Adventure and Blacksmiths. Maine Wildlife Park and Steamboat Landing Mini Golf are also worth visiting. Visit our Windham travel guide
View more Vacation Homes in Windham
Map
Windham, ME

What's nearby

  • An aerial view of a large body of water with multiple islands surrounded by dense forests.
    Sebago Lake
    2 min drive - 2.2 km
  • A building with 'L.L. Bean Inc.' signage, a large boot sculpture, and outdoor seating.
    LL Bean Flagship Store
    39 min drive - 59.3 km
  • Seacoast Adventure
    1 min walk - 0.1 km
  • Sebago Lake Basin
    2 min drive - 1.5 km
  • Maine Mall
    27 min drive - 37.4 km

Getting around

  • Portland Transportation Center
    28 min drive
  • Auburn, ME (LEW-Auburn - Lewiston Municipal)
    31 min drive

Restaurants

  • Starbucks
    3 min drive
  • McDonald's
    3 min drive
  • Dunkin'
    3 min drive
  • Dunkin'
    3 min drive
  • Applebee's Grill + Bar
    16 min walk

Frequently asked questions

Is The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! pet-friendly?

Yes, this property allows dogs (limit 3 total) with a maximum weight of up to 999 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks!?

Check-in begins at 4:00 PM.

What time is check-out at The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks!?

Check-out is at 11:00 AM.

Where is The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! located?

Situated in Windham, this vacation home is within 1 mi (2 km) of Seacoast Adventure, Sebago Lake, and Sebago Lake Basin. Jordan Bay and Little Sebago Lake are also within 2 mi (3 km).

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The Lookout on Pettingill Pond - waterfront, near Sebago Lake, hot tub, kayaks! Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 11 out of 17 reviews
Rating 8 - Good. 6 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

9.8

Cleanliness

9.8

Location

8.0

Property conditions & facilities

Reviews

Verified review

8/10 Good

Liked: Cleanliness, amenities, property conditions & facilities, communication
The house was beautiful and the lake is gorgeous. The morning views of the sun on the lake were stunning. The house was very clean and well stocked. We were a bit disappointed that the hot tub was a little run down, and there were swarms of insects under the cover so we couldn’t go in. But the pool table and game machine made up for it. Glenn was very communicative. A storm knocked out our power for a bit and caused some water pooling in the basement. Glenn was reachable immediately and offered to help. Overall a wonderful stay, and we’d definitely recommend!
Stayed 4 nights in Jul 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was clean, comfortable. The pond next to the house was very nice and made for a peaceful, relaxing atmosphere. Walkable to restaurants. We really enjoyed our time here.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property! So convenient
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay. This house in a convenient location with lots of stores, restaurants and available activities nearby. The house inside was beautiful with a peaceful view of the water. The open concept livingroom, diningroom, and kitchen was ideal for our family to be able to spend time together while on vacation.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Awesome scenery behind the house. Good restaurants nearby. Only 30-40 minutes from Downtown Portland. Easy check-in and check-out processes.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay!

What a wonderful house! She’s much bigger than at first glance and was perfect for our family of 7! My kids loved fishing on the pond. The busy highway was something to get used to but overall, we had a pleasant stay, thank you!!
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful seamless stay. Check in was easy, host left instructions around about how to use amenities, access WiF, etc. It was great to be right on a small lake, made for very peaceful coffee on the dock in the mornings. The property is right off a busy road - so if car sounds bother you it’s something to be aware of, but did not impact our stay. Great spot for trips to Sebago or downtown Portland.
View from the balcony
Stayed 3 nights in Jul 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall our stay was great. The house was clean and spacious. The view of the pond is gorgeous. We were able to quickly get in touch with the owner to troubleshoot an issue. I will note that the house is on a very busy road and it is quite loud, even inside the house.
Stayed 5 nights in Oct 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location
The home is beautiful. In the photos, it really doesn’t show from the view of the dock, how bad the water is. We thought that the kids would have been able to swim from the dock or play in the water - unfortunately, because of the moss/muck on the bottom, they weren’t able to at all. There was sand in the hot tub when we got there. The host was wonderful ensuring that it was taken care of right away so they at least had that to play in. The home was immaculate though, and our family had a wonderful time for this staycation. We appreciate how accommodating and centrally located the house was.
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house for families, we had a great time. Glenn is an amazing host, communication 10/10. There’s two kitchens and two laundry rooms which made everything easier for us. The grill and private beach area was also nice to have right by the water.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, listing accuracy
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Oct 2025