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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: 5

Osterville

Osterville Rental
Osterville retreat - now booking in 2026!
4BR
2 ½ baths
Sleeps 10

Long term rental available Sept 2025 - May 2026. $3,500-$4,500

Contact: Elizabeth, ID: 35972

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

Available for long term rental during off season peak months November 2025 - April 2026 for a price range between $6500 - $8000 depending on the lengt...

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 2025 - April 2026

Contact: RoseAnn, ID: 38500

Osterville - Barnstable Rental
Cape Escape with Beach pass- Last minute booking savings
3BR
2 baths
Sleeps 9

Rates start at $4,000/month for Feb - May 2026. For June 2026, the rate is $6,500. The monthly rate includes utilities (gas, electric, WIFI).Our 3-bed...

Contact: Noura, ID: 36837

Osterville Rental
Oasis in Osterville
3BR
2 ½ baths
Sleeps 7

Please inquire about possible long-term: $2,800 - 3,200/month

Contact: Marina, Sotheby's International Realty, ID: 40190