House holiday rentals in Winslow

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Popular amenities for Winslow house rentals

House rentals with a pool

Guest favourite
Home in Bangor
4.97 out of 5 average rating, 308 reviews

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

源尘Rating, 5 stars3 weeks ago
Nice place! I had a great time here with my dog. The host gave us instructions when we arrived, and he response very quickly and friendly. Highly recommend
Superhost
Home in Windham
5 out of 5 average rating, 5 reviews

Nature, Pool, Hot tub&Lakes! Mins to Sebago &More

KimRating, 5 stars2 weeks ago
We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!
Guest favourite
Home in Bangor
5 out of 5 average rating, 28 reviews

New Boho Cape with Pool! Fenced yard, pet friendly

CindyRating, 5 stars1 month ago
Thank you Christina! Great weekend stay for UMaine graduation. Great location from campus and stores for the things we forgot (haha).
Superhost
Home in Lincolnville
4.85 out of 5 average rating, 13 reviews

Coastal Retreat with Pool and Cheerful Vibes

AnneRating, 5 stars8 months ago
We felt like at home. The house is located in a private property with swimming pool and tennis courts. It’s very clean and very peaceful. Just a clarification about the description : there’s no bathroom in the basement. Then if you come with elderly people or very young kids, it could be annoying. If you like cooking, the kitchen is very well equipped. We´ll keep a very good memory of our stay in Ducktrap Retreat during the colorful foliage season.
Guest favourite
Home in Liberty
4.91 out of 5 average rating, 74 reviews

Luxe Liberty: Getaway with Heated Indoor Pool!

RitaRating, 5 stars1 week ago
What a wonderful experience! Rebecca was an absolutely outstanding host, always quick to respond and went above and beyond to ensure we had everything we needed. My family and I had such a peaceful stay. The home and location were incredibly tranquil, perfect for a relaxing getaway. The house and property were absolutely beautiful, and we loved sipping our morning coffee on the amazing balconies with the breathtaking views. There is so much space, and every room in the house is well thought out, functional, and cozy. The pool is even better than we hoped, so big and clean and in immaculate condition. We spent most of our time swimming and relaxing by the pool. We also enjoyed playing pool and having so many rooms to gather in with the comfort of plenty of new comfy furniture. Highly recommend for anyone looking to unwind for a vacation away from all the noise and chaos of daily life. Every single area was as described in the listing and better. Thank you for an unforgettable stay!
Guest favourite
Home in Mechanic Falls
5 out of 5 average rating, 19 reviews

Lovely home with hot tub and pool

AngelicaRating, 5 stars8 months ago
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!
Superhost
Home in Stonington
4.95 out of 5 average rating, 20 reviews

The Boathouse at Spruce Harbor

Janette Is pronounced as YanetteRating, 5 stars9 months ago
My return visit to the Boathouse was even lovelier than I hoped it would be. The location can't be matched by anything else I've seen. I enjoyed a September visit with my dog and was lucky to have pristine weather. I lived a very simple and healthy outdoors life and came home the better for it. The Boathouse is true to its description: it is simple and rustic and uncomplicated but well-equipped, and is perfect for one-and-dog, or for two people. A little coming-and-going from the neighboring houses meant that I didn't feel isolated. Margaret is truly an exceptional and friendly host who communicates promptly and clearly. I almost hesitate to share "my" Boathouse location with too many of my back-home friends because it feels so intimate and special. I already want to be back there. I offer my deep thanks to Margaret and to the place that I could - briefly - call home.
Superhost
Home in Washington
4.86 out of 5 average rating, 7 reviews

House in the woods

SavannahRating, 5 stars6 months ago
Booked this place for our anniversary to get away from the city for a weekend.. we found exactly what we were looking for! The hot tub was wonderful, the house was clean and cute, and we had everything we could have needed! Estelle was very responsive and gave clear instructions for everything. Would recommend this place for a quiet getaway or a small group trip in the summer!

Weekly house rentals

Top Guest favourite
Home in Oakland
4.9 out of 5 average rating, 96 reviews

Lake-House on water, East Lake, Near Waterville

LauraRating, 5 stars2 weeks ago
The location is gorgeous and peaceful, so close to the water so that we could enjoy it right out the window, or down at the dock. The weather was too rainy for paddling but we heard the loons. The space is comfortable and Mark had so many nice touches that made us feel welcome. We hope to be back!
Guest favourite
Home in Skowhegan
4.93 out of 5 average rating, 15 reviews

Cute house in town Skowhegan.

MichaelRating, 5 stars2 weeks ago
We really enjoyed our stay at Donald's house in Skowhegan. Only positive things to say: Exactly as described, clean, great location, easy access. Friendly and courteous host goes out of his way to be helpful. Would definitely stay here again, Mike from Nova Scotia
Top Guest favourite
Home in Oakland
4.94 out of 5 average rating, 72 reviews

Classy AF Home, walk across the street to Colby!

JessicaRating, 5 stars6 days ago
The photos don’t do this place justice! It is extremely pretty and bigger than I thought! Its location is perfect and made for an easy reunion weekend at Colby!
Top Guest favourite
Home in Rome
5 out of 5 average rating, 15 reviews

Newly built in 2024, Long Pond lake access

DanielRating, 5 stars2 weeks ago
We had a short two nights at Amy’s place. We stayed to attend our son’s graduation from Colby college. The school was about 32 minutes away from campus and the house worked out great. I’d love to return and stay longer in the future. Home and host were exceptional.
Guest favourite
Home in Belgrade
4.86 out of 5 average rating, 21 reviews

Family's Paradise: 3BR/2BA,Game Room & Lake Access

AnthonyRating, 5 stars3 months ago
Great rental property in a great place.
Top Guest favourite
Home in Canaan
5 out of 5 average rating, 11 reviews

Zeus's Landing| Lakefront | Close to Colby

BryanRating, 5 stars6 days ago
Great location and price for our group. Beds were comfortable and house was very clean. We will be staying here next year!
Top Guest favourite
Home in Brooks
4.98 out of 5 average rating, 94 reviews

Cozy New Home with Hot Tub: Cornerton

SamRating, 5 stars3 weeks ago
A wonderful little cottage. Peaceful, private and comfortable. I stayed for a night because I needed a break from moving and I didn’t want to be surrounded by all the boxes… between the hot tub and wicked comfy bed, I left the next day feeling far more capable of continuing to move furniture and unpack boxes. I will absolutely stay again when I need a break from my world for a night.
Superhost
Home in Liberty
4.76 out of 5 average rating, 21 reviews

House on Lake St. George

Mary BethRating, 5 stars10 months ago
Corie was so responsive with answers to questions about wifi and check-in to fun day trips we should try while we are there. The view of the lake is the best and the swimming was wonderful. Plus loved the paddle boat. Very relaxing!!

Private house rentals

Top Guest favourite
Home in Holden
5 out of 5 average rating, 31 reviews

Sunset Retreat on Brewer Lake

VanessaRating, 5 stars1 week ago
My husband and I really enjoyed our stay in Holden, ME! This Airbnb was so nice and clean and pretty close to Acadia National Park. I needed to stay close to work in the park and this spot was the perfect distance away. It was quiet, peaceful, and away from tourist traffic. Also close to gas stations and a grocery store. The hosts were so friendly and nice and we would highly recommend anyone stay here! Thank you Dana + family!
Guest favourite
Home in Canaan
4.8 out of 5 average rating, 30 reviews

Pond House

BarryRating, 5 stars1 month ago
We stayed for two months while I was on a temporary work assignment in the area. Check-in was simple, any questions were quickly answered. We had no problems with anything during our stay; everything was exactly as anticipated from the description. We immediately loved the view of the lake from the front windows! The kitchen was perfect, and we felt right at home. I was working long shifts, and a quiet, peaceful location was important for me to get enough sleep--this place provided it exactly. We were able to watch the lake go from ice covered when we arrived to open water when we left. We saw robins and loons arrive, and heard them calling as they settled into their summer homes. I would highly recommend this location to anyone who enjoys a quiet lake setting.
Superhost
Home in Burnham
4.85 out of 5 average rating, 67 reviews

The Maine Lake House with an Amazing Sand Beach!

AndreaRating, 5 stars1 month ago
The main house perfectly met our needs. The view to the lake was beautiful and the house was very clean. Beds were comfy (we did not use top bunks)
Guest favourite
Home in Greene
4.88 out of 5 average rating, 78 reviews

Beautiful Maine Lakeside Cottage

GeorgeRating, 5 stars2 weeks ago
Very clean and Host was very responsive, the setting matched the description 100%. Peceful sleeping with the water hitting the beach and the call of the Loon heard throughout the night. Can’t wait to return another day!!
Guest favourite
Home in Belgrade
5 out of 5 average rating, 9 reviews

River Front Maine Stay

TaylorRating, 5 stars1 month ago
Went for a fishing weekend with my brother. We were both very happy with the place. Boat launch for great pond was a 3 minutes drive and the boat launch for long pond was 7 minutes away which was nice so we could fish multiple lakes easily. Had dock access from great pond for the boat and was the end of channel that was well marked. We were able to dock the boat overnight there were no issues. A few places to eat nearby with access via boat (just a bit further up the channel with public dock behind the post office) and are also walkable. Clean space and great view. Beds were very comfortable for an Airbnb. Would recommend, great value, will stay here again if we come back to Belgrade.
Guest favourite
Home in Liberty
4.91 out of 5 average rating, 77 reviews

Modern Lake Front Home with Hot Tub

SherryRating, 5 stars1 week ago
Enjoyed our stay. The screened in porch was our saving grace due to rainy weather. Very relaxing trip!
Guest favourite
Home in Cornville
5 out of 5 average rating, 20 reviews

Modern Cornville Ranch

NeshaRating, 5 stars3 months ago
We stayed for 10 days while working in our cabin! We felt right at home, enjoyed all of the amenities, and would stay again!
Superhost
Home in Stockton Springs
4.79 out of 5 average rating, 39 reviews

Wildwood Acadia Salt House: 55 minutes from Acadia

ChelseaRating, 5 stars1 week ago
I had a lovely visit with a good friend. The air bnb stood out to us because of how beautiful the photos were and they didn’t do the place justice. It was so nice to stay in a place that felt like it was cut from a magazine. The home is in a private space but not far from restaurants and other towns with cute shops. We were close to lots of hiking trails and coastlines. I am quite sure I’ll be back!

Quick stats about house rentals in Winslow

  • Total rentals

    40 properties

  • Nightly prices starting at

    $15 AUD before taxes and fees

  • Total number of reviews

    680 reviews

  • Wi-Fi availability

    30 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

  • Local attractions

    Walmart Supercenter, Big G's Deli and Governor's Restaurant & Bakery

Destinations to explore

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