Apartment holiday rentals in Winslow

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Popular amenities for Winslow apartment rentals

Weekly apartment rentals

Top guest favourite
Flat in Dixmont
4.98 out of 5 average rating, 51 reviews

The Little House

jodyRating, 5 stars6 days ago
This clean and quiet cabin was really well appreciated. The morning coffee was perfect with cold cream in the fridge. Soft sheets and perfect pillows made for comfortable beds Judy is so hospitable and welcoming too!
Top guest favourite
Flat in Hope
4.98 out of 5 average rating, 45 reviews

Highfields Dahlia Farm

VictoriaRating, 5 stars2 weeks ago
I couldn’t ask for another place to stay at for vacation, it was a nice neighborhood close to all the attractions nearby. Roger also gave us higher quality food and drink contents instead of the cheapest options. Welcoming us in full arms and asked if we ever needed anything. If I was to plan another trip to Maine I would wait and see if Roger’s AirBNB was available. Thank you Roger for the great stay!
Guest favourite
Flat in Skowhegan
4.87 out of 5 average rating, 69 reviews

Upstairs apartment

EvanRating, 5 stars1 week ago
10-10 would recommend anytime great place to stay
Guest favourite
Flat in Madison
5 out of 5 average rating, 9 reviews

LeCabrera apartments rentals A Gem in small town

ElizabethRating, 5 stars2 weeks ago
Booked last minute for a work trip, and admit I did not look very closely at pictures when doing so. When I arrived, I was surprised to see such an adorable and perfect place. The decor is amazing, and the place is perfect. The kitchen and the bathroom are dream rooms, the shower is amazing and the kitchen is perfect and out of a magazine. Thank you for a wonderful stay, will def book again when traveling in Maine.
Top guest favourite
Flat in Hallowell
4.96 out of 5 average rating, 50 reviews

The Gallery

ElizabethRating, 5 stars7 months ago
Super cool space, artistically decorated, and comfortable for the two of us and our senior dog. The kitchen has a great layout for a small space, and was really fun to cook in. We hope to return soon!
Top guest favourite
Flat in Wilton
4.96 out of 5 average rating, 81 reviews

A Home away from Home.

KarenRating, 5 stars5 days ago
Linda and Bruce were fabulous host. The walking path down to the trout pond was enjoyable. The views outside were spectacular and you also had a great view from inside. I would definitely stay there again and bring my husband the next time. Thank you Linda and Bruce
Top guest favourite
Flat in Palermo
5 out of 5 average rating, 16 reviews

Valley View

LauraRating, 5 stars1 month ago
Marks place had everything needed for a long term stay. He and his dog Luna were friendly and didn’t mind the company of another dog. There was an unexpected amount of lady bugs in the home but Mark explained they are a constant battle in Maine and made suggestions on how to reduce/eliminate them as they got in. Highly suggest the meadery up the street. They use locally sourced ingredients and release their weekend menu each Thursday.
Guest favourite
Flat in Canton
4.96 out of 5 average rating, 23 reviews

Lakefront apartment near Western Maine mountains

CarrieRating, 5 stars6 months ago
We had a wonderful stay! Lisa is very responsive and so nice. We quickly made friends with Bella, the resident dog, and she is the sweetest pup. We were surprised with a Thanksgiving snow storm and the town lost power but there is a whole house generator, so we didn’t skip a beat or notice the power outage, which was so nice! There is a coffee pot on site (not a Keurig) and Lisa provided coffee grounds, which was amazing because we brought coffee pods. The bathroom is directly off the bedroom but there is no door, so if you need more privacy, I’d plan to tack up a blanket. The view of the lake is gorgeous and the property is peaceful. A gas station with a Dunkin is just a just a minute or two down the road and very convenient. We would definitely return.

Private apartment rentals

Superhost
Flat in Damariscotta
5 out of 5 average rating, 9 reviews

Private 1 BR Apt - 3 mi to town

RachelRating, 5 starstoday
It was a bit more than I like to pay, I’d probably have stayed a few more days, but I understand that it’s priced according to the market, and I’m sure she’ll get plenty more clients.
Superhost
Flat in Paris
5 out of 5 average rating, 70 reviews

Unbeatable Views & Privacy at Blank Slate Farm

KatherineRating, 5 stars1 week ago
SPACIOUS! Everything you could need, lots of fresh clean towels, TWO bathrooms(!!!) nicely appointed kitchen, extra blankets for our chilly rainy day, comfy couch with recliners.... Beautiful beautiful views and a back deck we relaxed on and watched the sunset. Private location nestled in the hills of Paris. We had the invitation to park the car in the garage so this would be super helpful in the winter! Very very pleased with our stay!
Superhost
Flat in Belfast
4.99 out of 5 average rating, 68 reviews

Coastal Loft with Beach Access

MelissaRating, 5 stars6 days ago
We had a very relaxing and peaceful weekend at Andrew’s place! The interior was gorgeous and comfortable, the backyard and path down to the water were so pretty and private. Andrew was super responsive, kind, and helpful. Belfast is an adorable little town, we would definitely go back.
Superhost
Flat in Bucksport
4.93 out of 5 average rating, 42 reviews

Penthouse Dynamic Water Views

DerekRating, 5 stars8 months ago
We had a great stay at the Penthouse! It was a perfect launching point for our downeast adventures in Acadia and points beyond. There was a beautiful waterfront view in a charming small town. The space was cozy, clean, modern and very comfortable for our stay. Highly recommend it.
Superhost
Flat in Northport
4.95 out of 5 average rating, 20 reviews

Lone Star Lodge - Newly Renovated Studio

JackieRating, 5 stars6 days ago
Definitely book this apartment for a cozy, peaceful retreat! Just as the pictures indicate, everything was updated and immaculately clean. But there is much more not included in the posting or pictures. Samantha provides the softest towels money can buy, night lights, a very comfortable bed, luxury soaps and lotions, and little welcome gifts. She also shares personalized recommendations in advance of your visit based on your interests. If I were to make any suggestions, a few more dishes in the kitchen would be helpful if there are more than two guests. But overall, this was one of the nicest rentals we have experienced thru any website, and we highly recommend.
Superhost
Flat in Augusta
5 out of 5 average rating, 11 reviews

Downtown 1BD | Sun-Filled | Spacious Apartment

SarahRating, 5 stars10 months ago
Easy-to-find location, beautifully designed apartment, squeaky clean kitchen, and a VERY comfortable bed. It is an older and creakier building, so you can hear the people above and around you, but it didn’t impact sleep. Heather was also accommodating to a last-minute late checkout, which was really appreciated. Highly, highly recommend.
Superhost
Flat in Edgecomb
4.86 out of 5 average rating, 485 reviews

Waterfront Condo at the Sheepscot

Maria JRating, 5 stars1 day ago
I can’t say enough about this cute condo right on the water! Easy to find and close to restaurants and historic sites, plus cute shops and art galleries. Audray was an amazing host and we will certainly be back!
Superhost
Flat in Rome
4.81 out of 5 average rating, 89 reviews

Belgrade Lakes/Wings Hill Lakeview Suite/Apartment

RahulRating, 5 stars8 months ago
It a great place. We enjoyed a lot and the lovely breakfast.

Apartment rentals with a hot tub

Superhost
Flat in Hallowell
4.83 out of 5 average rating, 173 reviews

3 bed up apt with no cleaning fee or checklist

EricRating, 5 stars7 months ago
Great stay. Would stay again.
Top guest favourite
Flat in Phippsburg
4.89 out of 5 average rating, 27 reviews

Quiet 2 bedroom apt close to beaches and town.

SamiRating, 5 stars9 months ago
I loved staying here! It was close enough to everything but yet it was secluded. Seeing the wildlife every day when we would leave really lifted our spirits. I 100% would stay here again.
Top guest favourite
Flat in Falmouth
4.91 out of 5 average rating, 200 reviews

Falmouth 3br near Town landing

EllenRating, 5 stars6 days ago
David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.
Top guest favourite
Flat in Standish
4.98 out of 5 average rating, 65 reviews

Sebago Retreat Suite

CorinneRating, 5 stars8 months ago
Susan’s place was the perfect spot for our getaway trip! The location and views were amazing and only a short trip to Portland. The space was spacious and exactly as pictured. We would stay here again.
Guest favourite
Flat in Topsham
4.87 out of 5 average rating, 549 reviews

Cozy hot tub haven

AshleyRating, 5 stars1 week ago
Wendy’s place was really nice and the hot tub is very private.. we definitely got our usage out of it… Wendy herself was extremely kind and open minded. She didn’t rush us out come check out, instead, she encouraged us to stay a little longer and enjoy the hot tub before our long journey back home.. she gave us good tips about golden gems only locals know about 🥰 She did have a cool book to share reviews but I didn’t have a pen.. also we left grape soda in the fridge from Canada for the next person to try!! Thanks again Wendy 5⭐️
Guest favourite
Flat in Brunswick
4.91 out of 5 average rating, 631 reviews

Downtown Hideaway-Loft HotTub Modern Clean Private

ColeRating, 5 stars1 week ago
Cute place! I enjoyed my stay. The hot tub was hot when I arrived, which I didn’t expect but highly appreciated!
Guest favourite
Flat in Carrabassett Valley
4.95 out of 5 average rating, 19 reviews

*New Listing* Sugarloaf Ski In/Out Condo

CameronRating, 5 stars1 month ago
Great place! Excellent location and not too far from the lift.
Top guest favourite
Flat in Lincolnville
5 out of 5 average rating, 14 reviews

Water Views - Beach Getaway - Private Balcony

HelenRating, 5 stars7 months ago
Perfect studio. Used the jetted tub, nice and relaxing. Lots of extras (new toiletries, coffee, filters, sugar, etc.) much appreciated and used. The view, esp at sunrise, was stunning. Quiet neighbors. The beach store (pizza, sandwiches, salads, coffee and more) was very good. Just down stairs and one building over. (get there early for their muffins) I would certainly stay here again.

Quick stats about flat rentals in Winslow

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹861 before taxes and fees

  • Total number of reviews

    670 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Winslow
  6. Flat rentals