Vacation rentals in Winslow

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Top-rated vacation rentals in Winslow

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Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 110 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.

Jan 30 – Feb 6

R2,261 ZAR per night

Guest favorite

Home in Augusta

5.0 out of 5 average rating, 11 reviews

Super cute waterfront cottage

Beautiful four-season waterfront cottage located on the outskirts of Augusta. The main living space has a full kitchen, living room/dining space, bathroom with laundry, and bedroom (queen bed). The walk-out basement offers a fantastic cabin-style space complete with its own bathroom) to lounge after a long day exploring. Or stay outside and enjoy the water views from the second-story deck or ground-level fire pit. Either spot is an amazing place to enjoy the night sky and listen to the loons.

Apr 27 – May 4

R2,540 ZAR per night

Guest favorite

Cabin in Skowhegan

4.82 out of 5 average rating, 401 reviews

The Cabin -Skowhegan

This guest house, main floor has living area, kitchen and dining area, 1 queen bed, with a daybed and trundler bed. Loft contains 2 twin beds. There is also a couch that could be used as a bed, full bathroom. Has no kitchen sink but has a kitchen area with microwave, large toaster oven, fridge/freezer, toaster and coffee maker, iron/board. Also has TV, DVD/blu ray player, Gas BBQ (May to November 1st.), as well as a picnic table, with benches and an out door fire pit and wood is supplied.

Oct 27 – Nov 3

R2,052 ZAR per night

Guest favorite

Home in Farmington

4.96 out of 5 average rating, 104 reviews

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

Jun 24 – Jul 1

R2,650 ZAR per night

Guest favorite

Home in Oakland

4.97 out of 5 average rating, 29 reviews

Quaint Little Cottage

Clean, quiet, cozy, and includes extras that will make your stay a comfortable one. Located in the Belgrade Lakes region this home is nearby Colby and Thomas College, Maine General and NorthernLight Inland Hospital, centrally located between Waterville and Augusta, and 1 hour to the Maine coast as well as ski mountains. Enjoy hiking, fishing, exploring Maine, and more! For great dining options your commute is 10 minutes, or you can stay in and have delivery from one of our local eateries.

May 4 – 11

R2,999 ZAR per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Mar 17 – 24

R1,864 ZAR per night

Guest favorite

Cabin in Mercer

4.95 out of 5 average rating, 189 reviews

Haven Hill Homestead Cabin #1

We are located in the beautiful area of central Maine with amazing views that bring peace to the heart and calmness to the mind. We live away from town on a quiet dirt road with no street lights. We have beautiful views of North Pond and we have wonderful sunrises! We have a small hobby farm and guests can visit the animals if wanted. We are proud to be a pet loving environment. It is very peaceful here. We guarantee that you will have a memorable stay here at Haven Hill.

Jun 11 – 18

R2,466 ZAR per night

Guest favorite

Home in Waterville

4.8 out of 5 average rating, 142 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 .

Feb 21 – 28

R2,557 ZAR per night

Guest favorite

Home in Appleton

4.96 out of 5 average rating, 122 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

May 21 – 28

R2,701 ZAR per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 1 – 8

R1,559 ZAR per night

Guest favorite

Apartment in Waterville

4.99 out of 5 average rating, 150 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.

Jun 22 – 29

R5,071 ZAR per night

Guest favorite

Guesthouse in Unity

5.0 out of 5 average rating, 192 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.

Oct 25 – Nov 1

R1,864 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winslow vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winslow's top sights

Walmart Supercenter4 locals recommend

Big G's Deli8 locals recommend

Governor's Restaurant & Bakery3 locals recommend

Ming Lee5 locals recommend

Mainely Brews Restaurant and Brewhouse19 locals recommend

Waterville Opera House17 locals recommend

Other great vacation rentals in Winslow

Guest favorite

Cottage in Oakland

5.0 out of 5 average rating, 95 reviews

The Rocky Road Camp on East Pond

Nov 4 – 11

R2,946 ZAR per night

Guest favorite

Home in Oakland

4.95 out of 5 average rating, 87 reviews

The Modern Maine Retreat

Dec 13 – 20

R4,583 ZAR per night

Guest favorite

Apartment in Oakland

5.0 out of 5 average rating, 26 reviews

Central Maine Loft Offering 4 Seasons of Fun

Jul 28 – Aug 4

R2,326 ZAR per night

Guest favorite

Cottage in China

4.86 out of 5 average rating, 35 reviews

Beautiful and Relaxing China Lake Sunset Cottage

Apr 27 – May 4

R2,115 ZAR per night

Guest favorite

Apartment in Palermo

4.98 out of 5 average rating, 88 reviews

One bedroom apartment in rural Waldo County, Maine

Oct 4 – 11

R1,787 ZAR per night

Guest favorite

Home in Oakland

5.0 out of 5 average rating, 54 reviews

Cute 2-bedroom home in convenient central location

Oct 6 – 13

R3,228 ZAR per night

Guest favorite

Apartment in Waterville

5.0 out of 5 average rating, 20 reviews

Rustic Charm on the Third Floor

Jul 2 – 9

R3,514 ZAR per night

Guest favorite

Apartment in Skowhegan

5.0 out of 5 average rating, 17 reviews

Cozy, cute, new, tiny duplex

Sep 7 – 14

R2,437 ZAR per night

Show all

Quick stats about vacation rentals in Winslow

Total rentals	50 properties
Rentals with dedicated workspaces	20 properties have a dedicated workspace
Pet-friendly rentals	10 properties allow pets
Family-friendly rentals	20 properties are a good fit for families
Total number of reviews	1K reviews
Nightly prices starting at	R190 ZAR before taxes and fees

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 10 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 apartment rentals in Winslow have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Winslow. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Winslow?
Four-legged friends are welcome in Winslow. Choose from more than 10 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Winslow?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, 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 $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Winslow

Top-rated vacation rentals in Winslow

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Winslow vacation rentals

Stay near Winslow's top sights

Other great vacation rentals in Winslow

Cottage in Oakland

Home in Oakland

Apartment in Oakland

Cottage in China

Apartment in Palermo

Home in Oakland

Apartment in Waterville

Apartment in Skowhegan

Quick stats about vacation rentals in Winslow

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do apartment rentals in Winslow have free parking?

Are there family-friendly vacation rentals in Winslow?

Do apartment rentals in Winslow have a kitchen?

Are there vacation rentals with a dedicated workspace in Winslow?

Do apartment rentals in Winslow have wifi?

Are there pet-friendly vacation rentals in Winslow?

What are the most popular amenities for House Rentals in Winslow?

How much does it cost to stay in house rentals in Winslow?

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