Winter Rentals

Browse all winter rentals available in Southern Maine below. /http://contact-us to schedule a showing or if you have any questions. Create an account to save your favorite winter rentals and to receive email notifications when similar rentals become available. 

York, ME

Price$10,500

Est. Mortgage: $/month

Listing Number RLW-WIL

  • Non-MLS Vacation Rentals
  • Bedrooms 6
  • Bathroom 5

Availability:Off-Season Getaways Winter Season 2009 - 2010 Luxurious setting for the whole family for your fall-winter escape. Holidays in Maine are bringing home a traditional flair with the experience of this incredible new home in York Harbor area. This newly built 6,300 square foot Georgian Colonial is York's premier rental offering. Lounge by the heated lap pool or on the rotunda deck to enjoy the spectacular views and harbor and ocean activities. Once inside you will find an elegant and tastefully furnished home. The exquisite European kitchen features granite counter-tops, convection oven, two dishwashers and two cook stoves. The family room invites gatherings by the thirteen foot high fireplace, one of six. Two master bedrooms, each with fireplace, king-sized beds and sitting area allow families the ultimate in privacy and luxury. The additional bedrooms offer pillow top queen beds. Baths include steam showers with multiple shower-heads flanked by Italian rounded glass. Enjoy a gentle rain forest shower or soak in the Jacuzzi with a hydra-massage. This fabulous retreat is close to beaches, boating, shopping and day trips to the mountains, Boston or Maine's expansive coastline. Accommodations for twelve people provides the perfect family retreat.

Listed by Anne Erwin Sotheby's International Realty

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Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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York, ME

Price$7,500

Est. Mortgage: $/month

Listing Number RLW-OSL

  • Non-MLS Vacation Rentals

Availability: Winter Season 2014-2015 Absolutely stunning oceanfront luxury vacation home available this fall/winter/spring season for weekly rent located in beautiful Cape Neddick, Maine. This magnificent home will not disappoint! Shingled English cottage style house, settled within a rocky cove, offers views of the Nubble Lighthouse, and a front row seat to the Atlantic Ocean. The home includes three bedrooms, including first floor master suite with en suite bathroom, high-end gourmet kitchen with six-burner gas Viking range, two sinks, Sub Zero refrigerator, coffee nook, eat-in area with fireplace, living room with coffered ceiling, majestic fireplace, and black walnut paneled walls. The lower level includes a reading room, exercise room, and office area. Outside are multiple stone terraces and places to find solace while listening to the sounds of the ocean. Located off of Route 1, Cape Neddick is part of historical York, Maine, an upscale coastal community abundant with opportunities for recreation, relaxation and amusement. The area boasts some of the finest beaches in New England. Other amenities include central air conditioning, two-car garage, outside shower, gas grill, multiple window seats with ocean vistas, soaking tub, Internet, cable TV, linens, washer/dryer, and pebbly beach just a short stroll from the home. Bedrooms Bedroom #1: First Floor master suite with bathroom, king-sized bed, window seat, and cable TV Upstairs Bedroom #2: Two twin beds, two closets, ceiling fan, and cable TV Bedroom #3: Queen sized bed, en suite bath with soaking tub, window seat, cable TV Rental Info Breakdown: Weekly Rent: $7,500 Security Deposit: $2,000 Tax: 8% Cleaning Fee: $400 Pets: Negotiable with additional Pet Fee

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Gorgeous York Harbor Home

York, ME 03909

Price$3,200

Est. Mortgage: $/month

Listing Number RLW-HOWELL

  • Non-MLS Vacation Rentals

Available September 15, 2017 - May 15, 2018 Gorgeous York Harbor home available this winter season. The first floor of this two storied, 2200sf home includes a laundry room with half bath, gorgeous kitchen with propane cook top and gas fireplace, dining area, and large living room with gas fireplace. The second level is comprised of four bedrooms and three bathrooms. A one car garage and automatic generator make winter a little easier! Bedroom Breakdown: #1: Queen, skylight #2: Queen, skylight #3: Two twins, en suite 3/4 bathroom #4: Master bedroom with gas fireplace, walk in closet, full bathroom, and balcony The tenant is responsible for all utilities (heat is oil, FHW), plus plowing. A credit check ($25/pp), security deposit, first month's rent, and renter's insurance is required. No pets, no smoking please.

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Dunelawn Winter Rental

39 Dunelawn Drive, Ogunquit, ME 03907

Price$3,000

Est. Mortgage: $/month

Listing Number RLW-GUNN

  • Non-MLS Vacation Rentals
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,000

Available October - June. Beautifully renovated carriage house in the well landscaped, gated, and private, but superb central location of Ogunquit. There is no better location than the Dunelawn- a five-acre, historic property on Ogunquit Beach/tidal river and the center village of Ogunquit. Once an old mansion has now been converted to 9 condos, 16 later-constructed townhouses and 4 two-floor units in the historic carriage house, where this unit is located. The 2000 square foot home offers two large bedrooms (one king and one queen) on the lower level each with an ensuite bathroom and walk-in closet. Upstairs you'll find an open concept living with vaulted ceilings and a well appointed kitchen with wine cooler and soap stone granite counters. Enjoy relaxing watching the sunrise or barbecuing on the patio with ocean views. No pets. Tenant is responsible for electric - water, sewer, and cable is included. A credit check ($25/pp), security deposit, first month's rent and renter's insurance required.

Listed by Jenna Reynolds of Anne Erwin Sotheby's International Realty

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Anne Erwin Sotheby's International Realty
19 Beach Street
PO Box 1188
Ogunquit ME, 03907
Office: 207-646-8802

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$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Pop's Cottage - a seaside retreat at Sea Point Beach!

Kittery, ME 03905

Price$2,600

Est. Mortgage: $/month

Listing Number RLW-HELD

  • Non-MLS Vacation Rentals
  • Bedrooms 2

Available for Full Weeks/Long Weekends or by the Month (see rates below): Located on Sea Point Beach, Pop’s Cottage (built in c. 1900) welcomes you this winter season with repurposed style and loads of character! Lovingly restored, this home is truly a hidden gem scattered amongst the likes of beautiful Maine beaches, ruins of historic forts and parks, and nearby Kittery Foreside with it’s delicious restaurants and charming shops. This lovely cottage features a stunning kitchen, making use of upcycled wood, an antique soap stone sink, new appliances & gas range, center island for seating, and views of the gorgeous Atlantic Ocean. A dining room connects to the deck with a gas grill for a true New England style BBQ with the salty ocean breezes washing away any of your daily worries. There is a “secret” loft area for the kids with two twin beds & play area promise plenty of extra room. Three bathrooms (a full, a 3/4, and a half bath) and easily the most incredible location in Southern Maine make this an incredible place to spend in Maine! Bedroom #1: Queen with en suite 3/4 bathroom Bedroom #2: Two twins (or King if pushed together) Additional Sleeping: Kid's loft with two twins Trundle bed in family room (two twins) No pets, no smoking please. Rates* Full Week: $1,000 Three Nights (Minimum): $250/night Full Month (includes all utilities): $2,600 *There is also a security deposit, cleaning fee, and 9% tax  

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

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Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Rita's Place - Winter Rental ALL UTILITIES INCLUDED!

York, ME 03909

Price$2,500

Est. Mortgage: $/month

Listing Number RLW-HOFF

  • Non-MLS Vacation Rentals
  • Bedrooms 5
  • Bathroom 4

Available October 1, 2018 - March 31, 2019 "Rita's Place", a spacious contemporary winter rental, just one row in from Long Sands Beach. This expansive home, with over 4,000 square feet of living space and fantastic ocean views from almost every room, includes a chef's kitchen with blue bahia granite countertops, custom trim, dishwasher, double oven, and gas cook top range. The first level also offers a living room with large TV, office space, and a ¾ bathroom with stacked washer/dryer. The second level is comprised of two bedrooms and another full bathroom, plus game room with pool table/TV/bar area. On the third floor resides the large master suite with TV, gas fireplace, and balcony, along with enormous master bath with tub and large, walk-in shower. Another full washer/dryer is found on this level, along with a full bathroom, a sitting room to relax, and two other bedrooms. No pets (non negotiable), no smoking. Rent is $2,500/month and includes everything. Garage is not usable. A credit check ($25/pp), Security Deposit ($2,500), First Month's Rent, and Renter's Insurance required. *Small apartment attached to home rented separately (separate entrance/driveway).  

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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York, ME 03902

Price$2,500

Est. Mortgage: $/month

Rented

Listing Number RLW-OMAL

  • Non-MLS Vacation Rentals
  • Bedrooms 5
  • Bathroom 4

Available: Winter Season 2018-2019 ALL UTILITIES AND PLOWING INCLUDED in this five bedroom ocean front home located on Shore Road in Cape Neddick, Maine for the winter rental season. Enjoy three season in New England while watching the mighty Atlantic as your backdrop. The home has a reverse set up - all but one bedroom are located on the first level. The master bedroom has a en suite bathroom and sliders to the patio.The upstairs is comprised of a large, open space - with great eat-in kitchen, dining area, and two lounging areas. Paying one check a month takes the guess work out of utility budgeting! A credit check ($25/pp), Security Deposit, First Month's Rent, departure cleaning fee of $300, and Renter's Insurance policy is required. A pet may be considered with additional pet deposit/agreement. *Linens are not included. A small apartment over the garage is rented separately.

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Great Winter Rental One Row in From Long Sands Beach

York, ME 03909

Price$2,500

Est. Mortgage: $/month

Listing Number RLW-VENE

  • Non-MLS Vacation Rentals
  • Bedrooms 5

Available September 1, 2018 - May 31, 2019 Just one row in from Long Sands Beach, this five bedroom, three bath rental will make a wonderful place to call home for this upcoming winter season. A bedroom with 3/4 bathroom, fireplaced living room, den, half bathroom, spacious eat-in kitchen and two dining areas are part of the accessible first floor, with plenty of space for each and every person to find a comfortable spot to relax. The upstairs includes four bedrooms and a full bathroom. Bonus attached garage and fenced-in yard - a pet may be negotiated with pet deposit/agreement. A tenant is responsible for heat (oil), gas, electricity, and plowing (small driveway). The cable and water is included. A credit check ($25/pp), first month's rent, security deposit, and renter's insurance is required.  

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Spend the Winter Season in this Amazing Kittery Point Home!

Kittery, ME 03905

Listing Number RLW-CRAWF

  • Non-MLS Vacation Rentals
  • Bedrooms 3
  • Bathroom 2

Available Winter Season 2018 - 2019 Come experience the picturesque waterfront along Chauncey Creek in Kittery Point, Maine this winter season. The home has a breezy open floor plan with sliding doors that take you to the flagstone patio or mahogany deck. The house sits high with fabulous water views and boasts a light and bright interior. A gourmet kitchen with mahogany countertops, gas stove, farmers fireclay sink, subzero refrigerator and new Bosch dishwasher are all the chef needs on vacation.  The pristine property comes with waterfalls, fabulous gardens, many decks, and exceptional craftsmanship. There are three bedrooms and two full bathrooms. Freshly painted inside, with new furniture on the way (photos to be updated soon!). A pet may be negotiated with additional pet deposit/agreement. A tenant is responsible for all utilities plus plowing. A credit check ($25/pp), a security deposit, first month's rent, pet deposit/agreement (if necessary), and renter's insurance is required.

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Winter Rental in York Harbor - Near Wiggly Bridge

York, ME 03909

Price$2,200

Est. Mortgage: $/month

Listing Number RLW-HOFER

  • Non-MLS Vacation Rentals
  • Bedrooms 5
  • Bathroom 3

Available Winter 2018-2019 This beautiful 5 bedroom home in popular York Harbor, Maine is available this winter season. Enjoy three seasons in a wonderful area of York - close to York Village and many of the beautiful seaside locations, such as: Harbor Beach, Fisherman’s Walk, The Wiggly Bridge or Steedman Woods. The home has three levels of living, with a first floor eat-in, renovated kitchen, formal dining room, laundry room, bathroom, living room, and a wonderful enclosed, three-season porch overlooking Barrells Mill Pond. The second level has three bedrooms (the master includes an en suite bathroom) and a full bathroom in the hallway. The third level is comprised of two more bedrooms. A detached two car garage is great for the snowy, winter months. No smoking on property. A tenant is responsible for all utilities except water and sewer. Lawn care is also included, but a tenant is responsible for plowing. A credit check of $25/pp, plus a security deposit, first month's rent, and renter's insurance is required. A dog may be negotiated with additional pet deposit/agreement.

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Simpson Lane

York, ME 03909

Price$2,160

Est. Mortgage: $/month

Rented

Listing Number RLW-WAL

  • Non-MLS Vacation Rentals
  • Bedrooms 5
  • Bathroom 4

Availability: Winter 2017-2018 (early September until end of May) A rare find in a desirable York Harbor, Maine winter rental. It's cottage comfortable, it's what relaxing in Maine should be all about. Settle in for the winter season starting early September. Spend a lazy afternoon on the sun deck watching the boat activity in the harbor - walk to the nearby Harbor Beach or access the Fisherman's path for a walk along the sea-side. Inside the home is a comfortable, spacious first floor with 2 living room areas, 1/2 bath, a large dining room, eat-in kitchen with stunning views and a sun-porch. Upstairs there are four quintessential cottage style bedrooms and two full baths. There is even a bonus third floor bedroom suite with 3/4 bath! A great fenced in yard with swing set and outdoor shower make it a great home for those warm months. A dog may be negotiated with additional pet deposit/agreement. The rent includes a landline, water/sewer, and cable/internet. The tenant is responsible for heat (heat is oil), electricity, lawn care (spring/fall clean up), and plowing (small driveway). A credit check $25/pp, security deposit, renter's insurance, and first month's rent apply. *A $300 cleaning upon departure is also required.

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Ocean Views and All Utilities Included in this beautiful Winter Rental

York, ME 03909

Price$1,900

Est. Mortgage: $/month

Listing Number RLW-HETT

  • Non-MLS Vacation Rentals

Available starting October 1, 2018 - May 31, 2019 ALL UTILTIES INCLUDED* Beautiful winter rental home on the 'Nubble' in York Beach, Maine. Located in between the famous Nubble lighthouse and beautiful Short Sands Beach, both just a short walk. The large corner lot provides plenty of space to enjoy outside activities. This beautifully decorated home features a large, bright, and airy master suite with king-sized bed, large closet and 3/4 bath. There are also two additional bedrooms, each with queen-sized beds, one on the main floor for easy access. You will find a spacious, fully-equipped kitchen with dining area. This house features a large 3/4 bath (walk in shower) with washer/dryer on the first floor and a full bath on the second floor. A credit check ($25/pp), Security Deposit, First Month's Rent, and Renter's Insurance is required. No pets (firm) and no smoking. Linens are not included and the garage is not usable. *Tenant is responsible for plowing/shoveling

Listed by Wendy Casey of Anne Erwin Sotheby's International Realty

{$office->Name}

Anne Erwin Sotheby's International Realty
31 Long Sands Road
York ME, 03909
Office: 207-363-6640

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Listing data is derived in whole or in part from the Maine IDX & is for consumers' personal, non commercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. ©2018 Maine Real Estate Information System, Inc. All Rights Reserved. equal opportunity housing logo   Privacy Policy

Anne Erwin Sotheby's International Realty participates in MREIS' Maine Internet Data Exchange (Maine IDX) program, allowing us to display other Maine IDX Participants' listings. This website does not display complete listings. Certain listings of other real estate brokerage firms have been excluded. Mortgage figures are estimates. Check with your bank or proposed mortgage company for actual interest rates. This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.