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Long-Term Vacation Rentals in Osterville

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: 7

Osterville

Osterville Rental
Osterville retreat - Just opened 2025 calendar!
4BR
2 ½ baths
Sleeps 10

Long term rental available Sept- May $3,500-$4,500

Contact: Elizabeth, ID: 35972

Osterville Rental
Quintessential Home Walk to Joshua's Pond Sleeps 10
4BR
3 baths
Sleeps 10

property available for long term rental during off season peak months November - April for a price range between $6500 - $8000 depending on the length...

Contact: Yara, ID: 39748

Osterville Rental
Private Oasis: Elegant Comfort & Free Beach Pass
4BR
3 ½ baths
Sleeps 9

$20,000 month in summer $12,000 - $15,000. September - April

Contact: RoseAnn, ID: 38500

Osterville - Barnstable Rental
Cape Escape with Beach pass- Summer 2025 Bookings Now Open
3BR
2 baths
Sleeps 9

Our 3-bedroom, 2-bathroom home is available for offseason monthly rental. It's perfect for those seeking longer-term stay (minimum of 31 days) to work...

Contact: Noura, ID: 36837

Osterville Rental
Dog Friendly Charmer - Convenient Location
3BR
2 baths
Sleeps 6

I am happy to rent the house for a long term rental between February and June. Price is $2,200 a month including utilities.

Contact: Erin, ID: 38319

Osterville Woods Rental
Osterville Great Family Rental!
3BR
3 baths
Sleeps 6

Off-season is $3000/ month inclusive of internet, cable and gas.

Contact: Ryan & Laura, ID: 35272

Osterville Rental
Cozy Osterville Retreat with Beach Pass
3BR
2 baths
Sleeps 6

Please contact the owner regarding a long term rental.

Contact: Nancy, ID: 39880