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Long-Term Vacation Rentals in Osterville

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).

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

# of Rentals: 7

Osterville

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

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

Contact: Elizabeth, Property ID: 35972

Spacious Home, Quiet Neighborhood, Great for Families
4BR
2 baths
Sleeps 10

Property is available October - May in the off-season for long term rentals. $3000-$4000 per month.

Contact: Michelle Fuller, Property ID: 37549

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, Property ID: 39748

Walking Distance to French Bakery/Beach Pass Provided
4BR
3 ½ baths
Sleeps 9

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

Contact: RoseAnn, Property ID: 38500

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, Property ID: 36837

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, Property ID: 38319

Osterville Great Family Rental!
3BR
3 baths
Sleeps 6

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

Contact: Ryan & Laura, Property ID: 35272