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Vacation rentals in Winslow

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Top-rated vacation rentals in Winslow

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Loft in West Gardiner

4.97 out of 5 average rating, 153 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Home in Starks

4.92 out of 5 average rating, 107 reviews

Autumn Getaway 4bd Farm Stay with Private Chef

Medicine Hill is a 125 acre farm on the Sandy river complete with an old fashioned swimming hole and an entire island to explore. We grow a wide variety of vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch taking it all in. 4 bedrooms have incredible views and are surrounded by trees or fields. And if the Chef is available..eat!

Home in Oakland

4.94 out of 5 average rating, 114 reviews

The Modern Maine Retreat

Stay at our Maine Getaway. Our fully renovated 1940s New Englander is sure to bring you peaceful vibes and luxury. Come play Pickleball with just a quick walk over to the courts, driving not necessary!Close to downtown Waterville, Colby College, Thomas College, UMaine Farmington. 2 min from Messalonskee Lake boat launch where you can boat, kayak, canoe, & ice fish. Proximity to ski mountains, Titcomb, Black Mountain, Sugar Loaf & Sunday River. Please note BBQ is only accessible May-October.

Cottage in Farmington

4.98 out of 5 average rating, 138 reviews

The cottage at Marble Farm.

This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

Rental unit in Belfast

4.98 out of 5 average rating, 303 reviews

Room with a Brew

Welcome to our new building. "A Room With a Brew" is located above Belfast's newest craft brewery, Frosty Bottom Brewing. A small community supported brewery open 2 days/week for 3-4 hours for beer share members. Guests can request a tour of the brewery and sample some fresh beer. Owners live in downtown Belfast and are available should any issues arise during your stay. The apartment/brewery is located 3 miles from downtown on a quiet road that offers local hiking and biking.

Cabin in Skowhegan

4.82 out of 5 average rating, 418 reviews

The Cabin -Skowhegan

Main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler. Loft has 2 twin beds. The couch could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large air fry oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/Blue ray player, Gas BBQ (May to November 1st.), as well as a picnic table, out door fire pit. For guest who are traveling by plane, towels are provided, upon request.

Yurt in Appleton

4.96 out of 5 average rating, 216 reviews

SILVER MOON, a Yurt for All Seasons

Silver Moon at The Appleton Retreat is quite private, check out the Trail Map. This contemporary yurt features a private therapeutic hot tub on the wrap around deck, a fire pit, and fast wifi. Silver Moon is located in a wooded area close to a bog that attracts a variety of wildlife. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Home in Waterville

4.82 out of 5 average rating, 171 reviews

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Cottage in Sidney

4.91 out of 5 average rating, 130 reviews

Waterfront Cottage

The Waterfront Cottage sits directly on the shores of Snow Pond, 15 minutes from Colby College and downtown Waterville and 1/2 mile from the Snow Pond Center for the Arts. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have a private outdoor hot soaking tub and water view barrel sauna. Paradise!

Home in Waterville

4.92 out of 5 average rating, 118 reviews

Sterling House

Updated 1950’s Cape in a quiet, centrally located neighborhood. We are licensed with the City of Waterville as a STR. Sleeps (7-8) comfortably. Less than two miles to Waterville’s Downtown area with several restaurants and bars, Waterville Opera House, Colby College, Thomas College as well as Inland Hospital and MaineGeneral Thayer Hospital. We are a pet-free home with no central A/C. Landscaping: We have a lawn service every other Wednesday between 7:30am and 9am.

Rental unit in Waterville

4.99 out of 5 average rating, 170 reviews

Sweet Retreat: 2 BDR Home Mins to Colby

Minutes from from Colby College (1.5 miles) , Inland Hospital (1 mile), Maine General (2 miles), Exit 127 on I-95 (5 miles). Forced air heat, WiFi, TV (Hulu & Netflix).The apartment is in a quiet, family friendly Waterville neighborhood on the second story of a two family home- has a private entrance, parking, two bedrooms (queen beds), one bathroom (full bath), dining area, fully equipped kitchen ( stove, oven, microwave), Screened in porch and patio.

Guesthouse in Unity

4.97 out of 5 average rating, 233 reviews

Modern Home on Working Farm

Modern duplex built recently across the street from a small berry and vegetable farm. This fully furnished home has a large deck with a great view. It is located 2.5 miles from Freedom village and the Lost Kitchen restaurant. It is also 8 miles from Unity College, and the Common Ground Fair fairgrounds. This single story building has a ramp, but it is slightly steeper then current standards. The inside is also laid out for wheelchair access.

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Popular amenities for Winslow vacation rentals

Free parking on premises

Air conditioning

Stay near Winslow's top sights

Colby College17 locals recommend

Colby Museum of Art45 locals recommend

Railroad Square Cinema21 locals recommend

Silver Street Tavern20 locals recommend

Mainely Brews Restaurant and Brewhouse19 locals recommend

Selah Tea Cafe17 locals recommend

Other great vacation rentals in Winslow

Cottage in China

5 out of 5 average rating, 30 reviews

Charming Private camp on China Lake

Cottage in Whitefield

4.96 out of 5 average rating, 74 reviews

Ollie's Cottage on the Sheepscot River

Cabin in Bingham

4.98 out of 5 average rating, 58 reviews

EcoCabin, for 2-4, 90 mi view

Cabin in Searsmont

4.98 out of 5 average rating, 65 reviews

Birch Hill Cabin w/Hot Tub

Rental unit in Pittsfield

4.89 out of 5 average rating, 82 reviews

Loft Retreat

Home in Oakland

4.96 out of 5 average rating, 52 reviews

Quaint Little Cottage

Rental unit in Waterville

4.91 out of 5 average rating, 11 reviews

Professionals Downtown Den | Sleeps 3

Cabin in Vassalboro

5 out of 5 average rating, 75 reviews

Webber Pond Cabin LLC

Quick stats about vacation rentals in Winslow

Total rentals
70 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi

Frequently Asked Questions

Do apartment rentals in Winslow have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Winslow. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Winslow?
Winslow has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Winslow have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Winslow. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Winslow?
Yes! Work meets play with ease at over 20 vacation rentals in Winslow featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Winslow have wifi?
Absolutely! We offer over 40 house rentals with wifi in Winslow. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Winslow?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with wifi, over 30 homes with a kitchen, over 30 homes with free parking, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Winslow?
Experience the best of Winslow with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Winslow have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Winslow. Enjoy a tailored experience with all the comforts you desire.

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