Winthrop Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19

Vacation Rentals in Winthrop

Escape to our cozy Winthrop cabin on Dexter Pond
Property grounds

Escape to our cozy Winthrop cabin on Dexter Pond

10.0 out of 10, Exceptional, (24)
"The cabin was so clean and welcoming. Our hosts were friendly and helpful. The views of the pond were wonderful. We were looking for a peaceful get away and it was just that! Will go back next year."
Escape to our cozy Winthrop cabin on Dexter Pond
Little Landing Cottage-gorgeous View BBQ Wi-fi
Suite | 1 bedroom, Internet

Little Landing Cottage-gorgeous View BBQ Wi-fi

3.5 star property
10.0 out of 10, Exceptional, (1)
"I love this little cottage. I will definitely be staying again. Thank you.!!!!!"
Little Landing Cottage-gorgeous View BBQ Wi-fi
Waterfront Cottage On Lake Cobbosseeconte
Property grounds

Waterfront Cottage On Lake Cobbosseeconte

9.6 out of 10, Exceptional, (16)
"We had a lovely stay. We would stay again if we come back to the area."
Waterfront Cottage On Lake Cobbosseeconte
Cozy Keyes Cottage-family-friendly Amazing Views
Suite | 2 bedrooms, iron/ironing board, Internet

Cozy Keyes Cottage-family-friendly Amazing Views

3.5 star property
Cozy Keyes Cottage-family-friendly Amazing Views
Cozy lake house on Sabattus Pond 2 bed 1 Bath
Property grounds

Cozy lake house on Sabattus Pond 2 bed 1 Bath

9.2 out of 10, Wonderful, (15)
"Perfect place to stay for a weekend "
Cozy lake house on Sabattus Pond 2 bed 1 Bath
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, (29)
"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
Blue Loon Camp on Pleasant Pond in Litchfield
Property grounds

Blue Loon Camp on Pleasant Pond in Litchfield

9.6 out of 10, Exceptional, (8)
"This comfy cabin can sleep 6 people no problem! With a close quarters experience made staying more the fun! EasyAccess to kayaks and canoes was awesome. Had a couple Beavers going back n forth in front of the cabin as well! Bailey the Neighbor dog stopped by to say hi in the yard along with Chancellor and Lous minutes prior. Thanks again for your accommodations. We would love to visit again in the future! "
Blue Loon Camp on Pleasant Pond in Litchfield
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 !
Cozy Long Pond Cottage: private mooring & shared dock
Outdoor dining

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (19)
"Very nice weekend and great host- very responsive!"
Cozy Long Pond Cottage: private mooring & shared dock
Lakeview Central Hub
Microwave, oven, stovetop

Lakeview Central Hub

8.0 out of 10, Very Good, (2)
"Beautiful place. Super quick communication. Quiet neighborhood. Loved it!"
The price is ￥24,507
￥52,383 total
includes taxes & fees
Oct 12 - Oct 13
Lakeview Central Hub
Waterfront 2br/2ba cottage
Fridge, microwave, oven, stovetop

Waterfront 2br/2ba cottage

9.8 out of 10, Exceptional, (15)
"This was a great place to stay, cental to places we wanted to see. Has water acess and lots of toy/boat options. Saw some loons, fireflies and the friendly free range chickens that would wonder around."
The price is ￥20,533
￥47,570 total
includes taxes & fees
Oct 15 - Oct 16
Waterfront 2br/2ba cottage
Sister A-Frame in Woods B
Exterior

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (6)
"Great stay. Would stay here again if in the area."
The price is ￥17,751
￥33,787 total
includes taxes & fees
Oct 13 - Oct 14
Sister A-Frame in Woods B
Lakeside retreat in Central Maine
Property grounds

Lakeside retreat in Central Maine

9.8 out of 10, Exceptional, (90)
"Paul & Kevin were so accommodating and Sailor Retreat was perfect. The home was clean, inviting and the perfect place for our visit. "
Lakeside retreat in Central Maine
Get in touch with nature.
Terrace/patio

Get in touch with nature.

10.0 out of 10, Exceptional, (29)
"Very peaceful and clean "
The price is ￥13,247
￥22,461 total
includes taxes & fees
Oct 8 - Oct 9
Get in touch with nature.
Large New Lakeside Cottage Central Air
Exterior detail

Large New Lakeside Cottage Central Air

8.4 out of 10, Very Good, (36)
"We loved the cabin, even in rainy weather. "
Large New Lakeside Cottage Central Air
Nature lovers Paradise your own island
Exterior

Nature lovers Paradise your own island

9.8 out of 10, Exceptional, (69)
"Amazing property! "
Nature lovers Paradise your own island
The Maine Experience: Where expansive nature meets modern comfort...
Property grounds

The Maine Experience: Where expansive nature meets modern comfort...

10.0 out of 10, Exceptional, (1)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
The price is ￥43,533
￥54,202 total
includes taxes & fees
Oct 14 - Oct 15
The Maine Experience: Where expansive nature meets modern comfort...
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, (15)
"Beautiful property, had everything that was needed. Would definitely book again!"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
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)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
The price is ￥22,121
￥33,113 total
includes taxes & fees
Oct 30 - Oct 31
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Lakefront Cabin
Fridge, microwave, oven, stovetop

Lakefront Cabin

10.0 out of 10, Exceptional, (27)
"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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winthrop Hotel Reviews

SureStay Hotel by Best Western Lewiston

SureStay Hotel by Best Western Lewiston

10/10 Excellent
"Easy access from the highwy, excellent breakfast, pet friendly, clean, comfortable, well appointed rooms."
Karen 1-night trip
Posted 4 days ago
SureStay Hotel by Best Western Lewiston

Find out more about Winthrop

Find out more about Winthrop

Search for holiday rentals in Winthrop on Expedia! You can easily find your home rentals, villas, holiday apartments in Winthrop using one of the methods below:

  • View our selection of featured holiday rentals in Winthrop
  • Use the map to find apartments and other holiday homes in the Winthrop neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winthrop while they last

Look no further and take a look at our great range of rental properties in Winthrop!

Frequently asked questions

Can I find a vacation rental in Winthrop?

Yes, we offer vacation rentals close to popular sights in Winthrop, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Winthrop?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: You might want to consider this vacation home rental near Winthrop, which is located in a rural location and has a hot tub, a barbecue grill, and air-conditioning 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.

How many vacation rentals are there in Winthrop?

Expedia has 17 vacation rentals for your stay in Winthrop.

What can I see and do in Winthrop?

Maranacook Lake and Cobbosseecontee Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Annabessacook Lake and Wilson Pond are other places worth a visit.

What are vacation rentals like in Winthrop?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Winthrop. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.