Winslow Vacation Rentals

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Sep 9 - Sep 10
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Sep 12 - Sep 14
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Sep 19 - Sep 21

Vacation Rentals in Winslow

Our top choices for Winslow vacation rentals

Spacious Country Home w/ Hot Tub, near Colby/Thomas
TV

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (28)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Property grounds

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
10.0 out of 10, Exceptional, (7)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Fridge, microwave, oven, stovetop

Large Secluded Cabin on the Lake - Now booking 2+ night stays

10.0 out of 10, Exceptional, (60)
"Canin was well stocked, easy to access. Perfect for what we needed. "
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Log cabin, King bed!!! Private beach!!
Smart TV, fireplace, DVD player, foosball

Log cabin, King bed!!! Private beach!!

9.8 out of 10, Exceptional, (31)
"Its a great place to relax and slow down."
Log cabin, King bed!!! Private beach!!
Large New Lakeside Cottage Central Air
Exterior detail

Large New Lakeside Cottage Central Air

8.2 out of 10, Very Good, (34)
"We loved the cabin, even in rainy weather. "
Large New Lakeside Cottage Central Air
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Property grounds

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

9.8 out of 10, Exceptional, (27)
"Wonderful stay, nice property, really enjoyed kayaking on the lake!"
$145 nightly
The price is $158
Sep 14 - Sep 15
Total with taxes and fees
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Central Maine Apartment offering 4 Seasons of Fun.
Property grounds

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (40)
"Very comfortable and clean VRBO!The hosts were very kind and easy to work with!!Great location for getting into Colby Highly recommend this location for people visiting in the area"
$209 nightly
The price is $228
Sep 15 - Sep 16
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (60)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, stovetop

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

10.0 out of 10, Exceptional, (13)
"Beautiful property, had everything that was needed. Would definitely book again!"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Lakefront Studio in the Trees with Gorgeous Views, Balcony, & Shared Canoe
Property grounds

Lakefront Studio in the Trees with Gorgeous Views, Balcony, & Shared Canoe

7.0 out of 10, Good, (8)
"Affordable and clean accommodations. View was lovely—will stay again!"
Lakefront Studio in the Trees with Gorgeous Views, Balcony, & Shared Canoe
Mountainside cabin "Sasquatch Haven"
Interior

Mountainside cabin "Sasquatch Haven"

9.4 out of 10, Exceptional, (23)
"Wonderful stay!"
Mountainside cabin "Sasquatch Haven"
Beachfront Cottage Nestled in a Cove
Terrace/patio

Beachfront Cottage Nestled in a Cove

10.0 out of 10, Exceptional, (2)
"Enjoyed our stay in the cottage. Loved the view of the lake. Nice to get away from it all and enjoy a relaxing few days on the water."
Beachfront Cottage Nestled in a Cove
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Interior

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

9.2 out of 10, Wonderful, (24)
"Had a wonderful time. Loon Cove is exactly that, the Loons were everywhere. The cabin was comfortable and well appointed. I really enjoyed my stay. I have one criticism, the sheer curtains in the bedrooms and bathrooms need to have a privacy/darkening option. The sun comes up at 4:30am and the trash guy, landscaper and nature viewers were on and around the property throughout my stay. "
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (83)
"What a lovely place! Incredible screened in porch, lots of beds and a quiet relaxing spot on the water. We didn’t receive any check in info until I inquired an hour beforehand but the hosts were quick to respond and it all worked great! Lots of places to hang out, took a canoe and kayak out on the water, a fantastic getaway for our family (even with me not reading carefully and not bringing our own sheets, hah!), we loved it and would stay again! "
Private and Calming Waterfront to the Rescue!
Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (64)
"Had another great time at Jenn and Brian's property. Exactly as advertised and Jenn is quick to respond to any questions. "
$488 nightly
The price is $532
Sep 10 - Sep 11
Total with taxes and fees
Lighthouse Lane
Sunset Chalet Lakefront Hot Tub Game Room
Dining

Sunset Chalet Lakefront Hot Tub Game Room

10.0 out of 10, Exceptional, (26)
"Great location, beautiful view, we've already talked about wanting to go back!"
$825 nightly
The price is $899
Sep 10 - Sep 11
Total with taxes and fees
Sunset Chalet Lakefront Hot Tub Game Room
New Waterfront Lake House - completed 2021
Outdoor dining

New Waterfront Lake House - completed 2021

10.0 out of 10, Exceptional, (27)
"We enjoyed our stay at this charming Belgrade lake house. The house was beautifully decorated, immaculate, and cozy for our week long stay while attending Colby graduation. Host was super organized, communicative, and provided everything we needed. Would definitely recommend staying here."
New Waterfront Lake House - completed 2021
on gorgeous Great Pond (lake), great for families!
Fridge, microwave, oven, stovetop

on gorgeous Great Pond (lake), great for families!

9.2 out of 10, Wonderful, (22)
"We've stayed at this cabin multiple times on our annual fishing trip. We love this place. Fantastic cabin, right on the lake with a great dock and fire pit. Erin is absolutely the best! So responsive and accommodating. To many positives to mention!Can't wait to come back again next year!"
on gorgeous Great Pond (lake), great for families!
Cabin China Lake
Exterior

Cabin China Lake

9.6 out of 10, Exceptional, (15)
"Beautiful and relaxing "
Cabin China Lake
Lakefront Cabin
Fridge, microwave, oven, stovetop

Lakefront Cabin

10.0 out of 10, Exceptional, (26)
"Enjoyed an awesome stay on the lake!! House was super and Kennith was a great host!"
Lakefront Cabin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winslow Hotel Reviews

Find out more about Winslow

Find out more about Winslow

Everything you need to know about Winslow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winslow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winslow vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winslow vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winslow. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winslow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winslow rentals

At Expedia, we put the best Winslow vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winslow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winslow vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winslow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Winslow?

Yes, you can find vacation rentals near well known sights in Winslow, or you can select a more secluded option if you're looking for relaxation. Winslow is known for its riverfront.

What are some of the best vacation home rentals that Winslow has to offer?

New Waterfront Lake House - completed 2021: This vacation home rental near Winslow is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Winslow?

Explore the area and family-friendly sights such as Maine State Museum, or get out into nature at a spot like Kennebec River. Fort Halifax and Waterville Opera House are a couple of places you'll find in the larger area.

What’s a vacation rental in Winslow like?

Vacation rentals are private properties you can book for several days or longer in Winslow. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.