Winthrop Holiday Rentals

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Holiday Rentals in Winthrop

Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (158)
"Incredible location, perfect choice for a small group to spend a little time on the lake shore."
Cottage on Cobbosseecontee Lake. Dates available.
Dog Friendly Cabin Right On The Water!!!
Exterior detail

Dog Friendly Cabin Right On The Water!!!

2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Fridge, microwave, oven, stovetop

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

9.6 out of 10, Exceptional, (25)
"Well kept with all the right amenities. Beautiful views."
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Lakefront Cottage - sleeps 6 - 2 baths
Property grounds

Lakefront Cottage - sleeps 6 - 2 baths

10.0 out of 10, Exceptional, (2)
"Great size, very clean. The posted pictures do not do this camp justice! Lots of upgrades and Beth is very responsive. Beautiful cove with little traffic. Sounds of loons day and night. Great bass fishing too! There is a wonderful dock but be sure to bring your own water toys. Great place for children with neighbors that encourage lots of kid play, exploring/adventuring, and boisterous fun."
Lakefront Cottage - sleeps 6 - 2 baths
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Fridge, microwave, stovetop, dishwasher

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

10.0 out of 10, Exceptional, (26)
"The property was as advertised! For a family with little kids, this was a great place to stay. David was helpful and very responsive!"
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Sunfish Cove is the perfect year round getaway.
Exterior

Sunfish Cove is the perfect year round getaway.

10.0 out of 10, Exceptional, (39)
"We had a great time staying at sunfish cove! Very spacious home with great views of the water! Really enjoyed the fire pit and the outdoor amenities!"
Sunfish Cove is the perfect year round getaway.
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

8.0 out of 10, Very good, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Lakeside retreat in Central Maine
Beach towels

Lakeside retreat in Central Maine

9.8 out of 10, Exceptional, (79)
"I can't explain the ease and how helpful the host was. We were traveling from a long distance for this. The host was helpful with late check in. The house was well maintained and clean everywhere. You get everything you need. The wifi is also fast. I wish they did provide some body wash and some extra stuff. No complaints at all. It was a memorable stay"
Lakeside retreat in Central Maine
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Aerial view

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

9.0 out of 10, Wonderful, (18)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Exterior

Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

10.0 out of 10, Exceptional, (56)
"Super cozy place. Use a silver popper on the pond"
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Interior

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

8.6 out of 10, Excellent, (14)
"We were traveling through New England and were looking forward to spending some time exploring the pond. We’d already been at the coast and were headed to more mountains and hiking inland over the rest of the week. We arrived and found they had put the paddleboards and kayaks away for the season. The neighbors on the cove still had lots of water toys set up. When we called, we were told that they put the Paddleboards and kayaks away October 1st. There was no mention of that in the listing and...
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards
Property grounds

Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

9.8 out of 10, Exceptional, (24)
"Roxie was a cozy tiny cabin! It was absolutely perfect for the one night passing through with the dog. My only regret was not having more time to make it a longer stay. The cabin has everything you need for a stay! The wood stove did a great job heating it, and it stayed pretty warm all night. GPS took me right there, no issue finding the road. And while no WiFi, cell service was fine and could stream playoff baseball before bed. Would 10/10 stay again and for longer if back in the area! "
The price is AU$246
includes taxes & fees
24 Nov - 25 Nov
Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Property grounds

5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE

10.0 out of 10, Exceptional, (4)
"The house had a lot of room. This would be a great family getaway place. The host was available and very attentive. I would recommend this house. "
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Year-Round Lakeside Retreat
Property grounds

Year-Round Lakeside Retreat

9.2 out of 10, Wonderful, (20)
"We only had a couple of hiccups with the heat upon arrival and a small electrical issue, but the host communicated quickly and all was resolved without further inconvenience to our family. Clean. Beds were very comfortable. Kitchen was well stocked. Overall we had a great stay, would stay again, and recommend to others! "
Year-Round Lakeside Retreat
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (75)
"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "
Private and Calming Waterfront to the Rescue!
Sunset Chalet- Stylish Waterfront Gem
Dining

Sunset Chalet- Stylish Waterfront Gem

10.0 out of 10, Exceptional, (23)
"We loved the Sunset Chalet! Very comfortable and all of the welcoming goodies & fresh flowers! We enjoyed our short but sweet stay! Beautiful view of the stream surrounded by the best smelling pine trees! The host was wonderful & very welcoming! Cant wait to visit again! sweet stay! "
The price is AU$1,243
includes taxes & fees
24 Nov - 25 Nov
Sunset Chalet- Stylish Waterfront Gem
Central Maine Apartment offering 4 Seasons of Fun.
Miscellaneous

Central Maine Apartment offering 4 Seasons of Fun.

10.0 out of 10, Exceptional, (32)
"This clean, spacious, comfortable place was just what we needed for our time spent in Maine. Gary and Irma thought of everything! "
The price is AU$393
includes taxes & fees
23 Dec - 24 Dec
Central Maine Apartment offering 4 Seasons of Fun.
An Authentic Clean & Cozy Maine Homestay
Fridge, microwave, oven, stovetop

An Authentic Clean & Cozy Maine Homestay

10.0 out of 10, Exceptional, (54)
"Third time staying at this location, works out great for my yearly 10 day visit to this area."
The price is AU$317
includes taxes & fees
3 Dec - 4 Dec
An Authentic Clean & Cozy Maine Homestay
Nature lovers Paradise your own island
Exterior

Nature lovers Paradise your own island

9.8 out of 10, Exceptional, (65)
"Amazing property! "
Nature lovers Paradise your own island
Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok
Fridge, microwave, oven, stovetop

Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok

9.0 out of 10, Wonderful, (18)
"This was just what we needed. Right on the water, quiet surroundings and the neighbors were so nice they brought us fresh vegetables."
Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok
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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Other types of properties in Winthrop you may be interested in

Dog Friendly Cabin Right On The Water!!!
Exterior detail

Dog Friendly Cabin Right On The Water!!!

2.0 out of 10, (1)
"The renter is not worth coming about the fact that her home is on a very steep hill. I told her I was a senior and had foot and ankle and knee surgeries and had a hard time walking. I saved up to rent a place all year. When I got there I had to call her to find out how to get to the lake. It is so steep I couldn't find an entrance to the lake, I finally found a foot wide muddy, slippery path which was 90 degrees straight up and down. I only took a few steps and realized I would break my neck if...
Dog Friendly Cabin Right On The Water!!!
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Fridge, microwave, oven, stovetop

Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit

9.6 out of 10, Exceptional, (25)
"Well kept with all the right amenities. Beautiful views."
Fantastic Lakefront Cabin W/ Free WiFi, Three Kayaks, Private Dock, & Firepit
Cottage on Cobbosseecontee Lake. Dates available.
Fridge, microwave, oven, stovetop

Cottage on Cobbosseecontee Lake. Dates available.

10.0 out of 10, Exceptional, (158)
"Incredible location, perfect choice for a small group to spend a little time on the lake shore."
Cottage on Cobbosseecontee Lake. Dates available.
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find a holiday rental in Winthrop?

Yes, there are holiday rentals close to the most popular sights in Winthrop, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winthrop has to offer?

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak: This holiday home rental outside of Winthrop is located on a lake, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Winthrop?

Expedia has 14 holiday 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 holiday rentals like in Winthrop?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winthrop. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for small groups.