Cabin
10.0(36 Reviews)
2 Bedrooms
5 Guests
Parking
Ocean View
Balcony/Terrace
View
US $299/Night
7 Nights - US $2,094
Winthrop Holiday Rentals
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Compare Villas, Resorts, & Rentals in Winthrop
10.0
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- View
Air Conditioner
US $663/Night
7 Nights - US $4,644
House
10.0(1 Review)
1 Bedroom
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $754/Night
7 Nights - US $5,278
House
10.0(32 Reviews)
2 Bedrooms
100 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $235/Night
7 Nights - US $1,648
House
10.0(3 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $561/Night
7 Nights - US $3,924
Cottage
10.0(14 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $582/Night
7 Nights - US $4,071
Apartment
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $543/Night
7 Nights - US $3,804
Cabin
9.8(29 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $531/Night
7 Nights - US $3,720
Cottage
9.8(22 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $396/Night
7 Nights - US $2,774
Luxury Holiday Rentals in Winthrop
Over 53+ Luxury Holiday Rentals in or Near Winthrop
House
10.0(15 Reviews)
5 Bedrooms
15 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $1,114/Night
7 Nights - US $7,798
House
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $952/Night
7 Nights - US $6,661
Cabin
9.8(10 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $907/Night
7 Nights - US $6,346
House
9.6(5 Reviews)
5 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
US $894/Night
7 Nights - US $6,257
House
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $668/Night
7 Nights - US $4,677
House
10.0(6 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $604/Night
7 Nights - US $4,225
House
3 Bedrooms
6 Guests
- Parking
- Internet
Pet Friendly
Security/Safety
US $531/Night
7 Nights - US $3,717
Cottage
10.0(4 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $462/Night
7 Nights - US $3,235
Cottage
9.4(8 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $462/Night
7 Nights - US $3,235
Pet-Friendly Holiday Rentals in Winthrop
Over 18+ Pet-Friendly Holiday Rentals in or Near Winthrop
Cabin
9.8(7 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,305
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Internet
- Pet Friendly
Sports/Activities
US $335/Night
7 Nights - US $2,345
Apartment
9.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $329/Night
7 Nights - US $2,304
US $381/Night
7 Nights - US $2,667
House
10.0(98 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $349/Night
7 Nights - US $2,442
House
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $318/Night
7 Nights - US $2,225
House
8.8(9 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $372/Night
7 Nights - US $2,602
Cabin
9.8(29 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $387/Night
7 Nights - US $2,706
House
9.0(4 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $292/Night
7 Nights - US $2,046
Large Holiday Rentals and Private Villas in Winthrop
Over 7+ Large Holiday Rentals and Private Villas in or Near Winthrop
House
3 Bedrooms
11 Guests
Child Friendly
US $429/Night
7 Nights - US $3,005
Villa
3 Bedrooms
8 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $433/Night
7 Nights - US $3,031
House
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $445/Night
7 Nights - US $3,117
House
3 Bedrooms
11 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $378/Night
7 Nights - US $2,648
Other
10.0(19 Reviews)
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $722/Night
7 Nights - US $5,055
House
4.6(14 Reviews)
4 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $618/Night
7 Nights - US $4,326
US $509/Night
7 Nights - US $3,563
Wheelchair Accessible Holiday Homes in Winthrop
Over 1+ Wheelchair Accessible Holiday Homes in or Near Winthrop
House
5.0(1 Review)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $261/Night
7 Nights - US $1,827
Winthrop Private Villas and Holiday Homes Under $200
Over 5+ Winthrop Private Villas and Holiday Homes Under $200
House
10.0(4 Reviews)
3 Bedrooms
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $199/Night
7 Nights - US $1,393
House
2 Bedrooms
4 Guests
Private Beach
Oceanfront- Parking
- Ocean View
US $194/Night
7 Nights - US $1,358
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $197/Night
7 Nights - US $1,377
Apartment
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $72/Night
7 Nights - US $502
Apartment
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $195/Night
7 Nights - US $1,365
Instantly Bookable Holiday Homes in Winthrop
Over 9+ Instantly Bookable Holiday Homes in or Near Winthrop
Apartment
7.6(4 Reviews)
1 Bedroom
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $270/Night
7 Nights - US $1,887
Cottage
1 Bedroom
3 Guests
- Child Friendly
Laundry
Bedding/Linens- Security/Safety
US $233/Night
7 Nights - US $1,633
House
9.6(8 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $359/Night
7 Nights - US $2,515
Cabin
2.0(1 Review)
2 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $282/Night
7 Nights - US $1,971
Cottage
9.6(16 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $509/Night
7 Nights - US $3,561
House
9.0(7 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $529/Night
7 Nights - US $3,703
House
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $639/Night
7 Nights - US $4,472
Cottage
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
US $212/Night
7 Nights - US $1,481
Cabin
9.8(6 Reviews)
2 Bedrooms
9 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $414/Night
7 Nights - US $2,899
Book a Last Minute Place to Stay in Winthrop
About Casai's Private Villas and Holiday Rentals in Winthrop
Discover more than 62 vacation rentals available in Winthrop. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winthrop.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winthrop, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winthrop. On average, places to stay near Winthrop offer 984.94 ft², with nightly prices averaging US $431.
With Casai, finding and comparing holiday rentals in Winthrop is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Winthrop, ME
There are 62 Winthrop, ME Holiday Rentals
- Prices for a holiday home in Winthrop start at US $186
- Top rated vacation home in Winthrop is Rustic, peaceful lake house on Lake Cobbosseecontee; free WIFI, ADA friendly.
- Most popular short term in Winthrop is Rustic, peaceful lake house on Lake Cobbosseecontee; free WIFI, ADA friendly.
- Cheapest place to stay in Winthrop is Cozy cottage in the Winthrop Lakes Area
- Most expensive holiday rental in Winthrop is Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Frequently Asked Questions About Winthrop?
What are the top holiday rentals in Winthrop?
With numerous options available in Winthrop, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winthrop:
- Rustic, peaceful lake house on Lake Cobbosseecontee; free WIFI, ADA friendly.
- Escape to our cozy Winthrop cabin on Dexter Pond
- Peaceful Fisherman's Paradise w/Deck + Fire Pit!
- Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
- Cozy Keyes Cottage | Lakefront Dock Kayaks
- Dock + Kayaks: Annabessacook Lake Retreat!
- ANNABESSACOOK WATERFRONT WITH DOCK
- NEW Construction! 2-BR Apt walking distance to The Barn at Silver Oaks, Winthrop
- Private, sandy beach on Lake Cobbosseecontee!
- Little Landing Cottage On Cobbossee Lake
Which holiday homes in Winthrop are best for families?
If you're searching for a family-friendly holiday home in Winthrop, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winthrop:
How many Casai.com holiday rentals are available in Winthrop?
As of 2026, Casai boasts over 62 properties listed in the Winthrop area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winthrop.
