Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.
   
  •  
    Locations
  •  
    Dates
  •  
    Price
  •  
    Bedrooms / Sleeps
  •  
    Proximity to Water
  •  
    Exterior Amenities
  •  
    Interior Amenities
  •  
    Area Amenities
  •  
    Green Amenities
 
Advanced Search
Locations
 
Locations
+ multiple towns
Click on an area of the map in order to see it in more detail.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Click the magnifying glass to zoom out.
Dates
 
Dates
Nights in Your Stay
If you have flexible arrival and/or departure dates, put the first possible arrival date and last possible departure date in the date fields above. We'll search for your number of nights in between
By Week (compare up to 4 weeks)
Pick your season
Tell Us More About Your Trip (optional)
Number of Weeks
Starting On What Day?
Search and compare up to 4 weeks in one season
Only 4 weeks may be selected at one time.
 
By Entire Months
Number of months
Pick the starting month
  • October
    2020
  • November
    2020
  • December
    2020
  • January
    2021
  • February
    2021
  • March
    2021
  • April
    2021
  • May
    2021
  • June
    2021
  • July
    2021
  • August
    2021
  • September
    2021
  • October
    2021
  • November
    2021
  • December
    2021
  • January
    2022
  • February
    2022
  • March
    2022
  • April
    2022
  • May
    2022
Price
 
Price
Any
Bedrooms / Sleeps
 
Bedrooms / Sleeps
Bedrooms
Clear
Sleeps
+
Proximity to Water
 
Proximity to Water
  •  (½ mi. or less)
    * ½ mi. or less
     (½ mi. or less)
Exterior
 
Exterior
Interior
 
Interior
Area amenities
 
Area amenities
Green amenities
 
Green amenities
 

Osterville is an exclusive seaside community on Nantucket Sound. Elegant waterfront homes, many of which were built in the 19th century, line the main streets.

3 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 8

Osterville
ID 27473
4 BR
2 baths
Sleeps 8
Recently renovated home, steps to Osterville Village!
Recently renovated home, steps to Osterville Village!
Distance to beach: 1 mile to Dowses Beach - beach sticker included
17 reviews read reviews
Summer:
$3,250/wk
Off Season:
$250 - $325/night
$1,300 - $3,100/wk

Osterville vacation rentals that sleep 7

Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Spacious Cape Cottage with English-Style Garden
Spacious Cape Cottage with English-Style Garden
Distance to beach: 4/10 mile to Joshua Pond and 1 mile to Dowses
25 reviews read reviews
Summer:
$2,800/wk
Off Season:
$1,440 - $2,300/wk

Osterville vacation rentals that sleep 6

Osterville
ID 32374
3 BR
2 ½ baths
Sleeps 6
Renovated Osterville Cape w/AC, 2 1/2 Baths, Near Village
Renovated Osterville Cape w/AC, 2 1/2 Baths, Near Village
Distance to beach: 1 3/10 miles to Craigville Beach and 1 6/10 miles to Dowses
Summer:
$2,700/wk
Off Season:
$325 - $350/night
$2,500 - $2,700/wk