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Long-Term Vacation Rentals in Orleans

A long-term rental is considered to be an extended stay of more than 31 days. 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). Massachusetts Landlord Tenant Laws will apply.

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

# of Rentals: 6

Orleans

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

October 2025 to May 2026 monthly rentals available. $3000 - $4000/mo.

Contact: Ruth, ID: 20703

Orleans Rental
5BR Retreat w/ Hot Tub, Firepit, Near Beaches, Dining, Golf!
5BR
2 ½ baths
Sleeps 8

Oct 2025 - May 2026 Off Season Monthly 2BD/2BA Rental $3,000 Monthly* *Incl. a landlord contribution of $350/month for utilities (electricity, propan...

Contact: Kristian & Justin, ID: 40785

Orleans Rental
Pleasant Bay with Private Beach Use
3BR
3 baths
Sleeps 6

Long term rental is available for 3 bedroom/3bath home from January 15th - April 15th 2026 at $5,000 a month. Proration for less than 30 days.

Contact: Tracy, ID: 35950

East Orleans Rental
Parson's Cottage
3BR
2 baths
Sleeps 6

$2,500 per month, includes all utility charges. Nov 1 - May 1 2026. Orleans location, opposite Nauset Farm Shop, 3-bed, 2-bath home, fully furnished a...

Contact: Richard, ID: 36644

East Orleans, Barley Neck Rd o Rental
East Orleans Old Cape Vacation Cottage
2BR
1 bath
Sleeps 6

Will consider off season rental, please contact us to discuss. $2600-2800 per month during the fall, winter, spring season. Summertime monthly rental ...

Contact: Patty Doshier, ID: 9996

East Orleans Rental
Cute Cape Cottage
2BR
1 bath
Sleeps 4

We will consider multi-month rentals from Oct 15 thru May 15 2026. Monthly rent will be about $1950-$2,200/month depending on length of time and utili...

Contact: Beth , ID: 28618