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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

GREAT FAMILY E.ORLEANS BEACH HOUSE 1.7 m NAUSET BEACH!
4BR
2 ½ baths
Sleeps 13

Long term winter rental available. Please contact me to discuss. Thank you.

Contact: Michael & Liz, Property ID: 23957

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

''Saltaire'' A Stunning Private Property W/Resort Amenities
5BR
2 ½ baths
Sleeps 12

32 Day Rentals Available for Saltaire during Summer 2020. Dates include June, July, August and September. From $20k to $40k for the extended month. Pl...

Contact: Kim, Property ID: 32168

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-May 15. Obviously it is fully furnished. The amount of rent somewhat depends on the # of peopl...

Contact: Kenneth, Property ID: 29075

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

The house has exquisite views north and west, is well-insulated, features two fireplaces, and is protected from easterly storms. Once snow falls, i...

Contact: Andrew , Property ID: 31120

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

No Winter rental 2020-2021

Contact: Kim, Property ID: 25214

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

This home will be offered as a two bedroom home at winter season (from Jan -April) for $1500 - Nov & Dec for $2000/mon plus all utilities. It is co...

Contact: Nina, Property ID: 9286

1.6 acres w/ private fresh & salt water access & rec room
4BR
2 ½ baths
Sleeps 10

Beginning in September, available for monthly rental (by law, taxes not collected if more than 32 days rented). $6000 per month; additional days pror...

Contact: Tom, Property ID: 7598

Special Monthly Spring Rates. Bay/Marsh Front.Walk to Skaket
4BR
2 baths
Sleeps 10

Rent by month off season. Available after 9/12 for $4,000/mo.

Contact: Laura, Property ID: 28723

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

January 2014 to May 2014 monthly rentals available. $3300 - $4000/mo. Please call Ruth or Phil at 917-405-8501 to inquire further.

Contact: Ruth, Property ID: 20703

Seasalt Orleans -New- 5 minute drive to Nauset Beach!
3BR
2 baths
Sleeps 9

Off season monthly rentals and shorter stays available. Please inquire.

Contact: Mary Ella , Property ID: 33655

Private fun house between Nauset and Skaket beaches
4BR
3 baths
Sleeps 8

Available monthly November-March. $3500 per month.

Contact: Penny, Property ID: 30951

3 BR Contemporary on Little Pleasant Bay with Private Beach
3BR
3 ½ baths
Sleeps 8

Winter rental available starting February 2020, $2,500 per month with aggressive pricing for multiple months.

Contact: Bill, Property ID: 32875

Crystal Lake Tranquility - Escape to the Cape this May
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

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

Available monthly off season: price ranges from $2000 per month to $5000. Call for more information.

Contact: Jim, Property ID: 28852

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

3-bed, 2-bath / pet friendly; Nauset Beach; Pleasant Bay
3BR
2 baths
Sleeps 5

$1,700/month + utilities, Nov-Apr. Month-to-Month lease.

Contact: Mark, Property ID: 29511

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

Available October - May $2500 per month Utilities Negotiable

Contact: John, Property ID: 27515

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

Escape the City this Winter we are offering Monthly Rentals this Winter $2500-2800 per month. Please reach out to discuss.

Contact: Cindy, Property ID: 31244

Private, In-town Orleans house with view of Boland Pond
2BR
1 bath
Sleeps 4

LT rentals considered.

Contact: Amy , Property ID: 31520

Cute Cape Cottage
2BR
1 bath
Sleeps 4

We will consider multi-month rentals from Oct 15 thru May 15. Monthly rent will be $1200/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