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Long-Term Vacation Rentals in Orleans

Rental homes are available for an extended stay of a month or more at a time. While some rentals by owner will be available for long-term stays during the summer or year-round, majority are available during the off-season (fall, winter and spring). Monthly prices may vary depending on the number in your party and length of stay.

Rentals are listed by location, sleeping capacity, and number of bedrooms.

# of Rentals: 22

Orleans

Executive Waterfront Luxury Estate; Heated Pool; 6000 Sq.ft.
4BR
6 baths
Sleeps 16

Experience Cape Cod at this 6000 sq.ft Luxury Waterfront estate /w heated pool. Offers long-term rentals in July and August. Inquire for detail quote ...

Contact: Alex, Property ID: 14224

Stunning Property with Private Pool and Walk to Ocean Beach
6BR
4 ½ baths
Sleeps 12

Off season rentals are available. Pricing assumes renter is responsible for utilities. Pool will be closed and outdoor furniture will be stored in the...

Contact: Robert, Property ID: 31175

Nauset Beach House - Big, Beautiful, Views, Walk To Beach!
4BR
3 ½ baths
Sleeps 12

This home is available for winter rental between Oct 15-April 1. Obviously it is fully furnished. The amount of rent somewhat depends on the # of peop...

Contact: Kenneth, Property ID: 29075

Bright waterfront haven with AC and heavenly 100° views
4BR
3 ½ baths
Sleeps 10

The house is not available for long-term rentals. It is, however, available for bookings of up to 30 days, and Fall, Winter, and Spring guests appreci...

Contact: Andrew , Property ID: 31120

Beautiful Nauset Beach 4 Br Home, A/C, Wifi, Slp 12
4BR
3 baths
Sleeps 10

This home will be offered as a one or two bedroom home at winter season (from Jan -March) from $1300 ; Nov & Dec & April from $1800/mon plus all util...

Contact: Nina, Property ID: 9286

Unique & Charming Renovated Barn-Walk To Private Beach
4BR
3 ½ baths
Sleeps 10

No Winter rental 2020-2021

Contact: Kim, Property ID: 25214

Sunny, Charming, Kid-Friendly, Updated Farmhouse
3BR
2 ½ baths
Sleeps 10

Winter 2022/2023 is booked, but we are opening our cozy Orleans Farmhouse up for 2023/2024 winter rentals. You may rent any amount of time, ranging fr...

Contact: Carrie, Property ID: 29389

Water views, private waterfront, 2.7 mi. to Nauset Beach!
3BR
2 baths
Sleeps 10

October to May monthly rentals available. $3000 - $4000/mo. Please call Ruth ( 917-586-3753) or Phil (929-810-8068) to inquire further.

Contact: Ruth, Property ID: 20703

3 BR Contemporary on Little Pleasant Bay with Private Beach
4BR
3 baths
Sleeps 8

Winter rental available starting February 2020, $3,500 per month with aggressive pricing for multiple months.

Contact: Bill, Property ID: 32875

Renovated Beautiful Home-Dog Friendly! NEW KITCHEN!
4BR
2 baths
Sleeps 8

Please contact owner directly.

Contact: Judy , Property ID: 35920

Upscale East Orleans Home- 5 minutes to Nauset Beach!
3BR
2 baths
Sleeps 8

Please inquire

Contact: Mary Ella , Property ID: 33655

Summer 2022.Waiting List. Late Summer/Autumn Availability
3BR
3 baths
Sleeps 8

We are renting multiple weeks throughout the year as available. 32 day leases are required to avoid the 14.45% Massachusetts Lodging tax.

Contact: Lynda, Property ID: 19124

Spacious cottage near Pleasant Bay with new outdoor sauna
2BR
2 baths
Sleeps 7

We will consider long-term (month +) rentals. However, due to its seasonal nature, we are required to shut our cottage down between November and Marc...

Contact: Gail McCullagh, Property ID: 12283

Charming Restored Cottage: The Summer House in East Orleans
3BR
2 baths
Sleeps 6

Available monthly off season: price ranges from $3,000per month to $5000. Call for more information.

Contact: Jim, Property ID: 28852

Peaceful Contemporary - On Private Wooded Lot
3BR
2 baths
Sleeps 6

Available for long-term winter rental.

Contact: Louis Morongell, Property ID: 32809

Two bedroom home with AC on luminous Crystal Lake
2BR
1 ½ bath
Sleeps 6

November to April. $3000/month; 6 month lease.

Contact: Kamesh, Property ID: 30757

Welcome to our Orleans Escape!
2BR
1 bath
Sleeps 5

Inquire

Contact: Cindy, Property ID: 31244

Mimi's House: 2 Bedroom Home w/a Firepit & Central AC
2BR
1 bath
Sleeps 5

Available

Contact: John, Property ID: 27515

Fish, Swim, Kayak (supplied) in safe, clean pond.
2BR
1 bath
Sleeps 5

Available for long-term winter rental from November to June. $5000 per month

Contact: Louis Morongell, Property ID: 28481

Delightful Cape Cod Cottage! Orleans Charm at it's Finest.
2BR
1 bath
Sleeps 5

Winter rental available December 1st 2021 to May 31st 2022 at a rate of $1,800 / mo + utilities.

Contact: Kara, Property Manager, Cape Peninsula Properties, Property ID: 34864

Cute Cape Cottage
2BR
1 bath
Sleeps 4

We will consider multi-month rentals from Oct 15 thru May 15. Monthly rent will be about $1850-$2,000/month depending on length of time and utilities....

Contact: Beth , Property ID: 28618

Cape Carriage House Getaway!
2BR
1 bath
Sleeps 4

For long-term winter availability, please contact us. $1200-$1500 per month

Contact: Outi and David Baker, Property ID: 20597