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
 
Advanced Options
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
  • April
    2019
  • May
    2019
  • June
    2019
  • July
    2019
  • August
    2019
  • September
    2019
  • October
    2019
  • November
    2019
  • December
    2019
  • January
    2020
  • February
    2020
  • March
    2020
  • April
    2020
  • May
    2020
  • June
    2020
  • July
    2020
  • August
    2020
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
 

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.

12 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 10

Osterville
ID 31391
Summer:
$450 - $650/night
$2,500 - $3,800/wk
Off Season:
$200 - $400/night
$1,400 - $3,000/wk

Osterville vacation rentals that sleep 9

Osterville
ID 32077
Summer:
$7,000/wk
Off Season:
$5,500 - $7,500/wk

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
11 reviews read reviews
Summer:
$2,700 - $2,900/wk
Off Season:
$250 - $300/night
$1,400 - $2,900/wk
Osterville
ID 27235
Summer:
$2,500 - $3,000/wk
Off Season:
$2,500/wk
Osterville Woods, Osterville
ID 32073
4 BR
2 baths
Sleeps 8
Ideal Osterville Vacation Home W/Ac, Ocean & Pond Beach Pass
Ideal Osterville Vacation Home W/Ac, Ocean & Pond Beach Pass
Distance to beach: 1.8 mi to Joshua Pond and 3.8 mi to Dowses
Summer:
$2,975/wk
Off Season:
$2,350 - $2,975/wk
Osterville
ID 24368
Summer:
$300 - $400/night
$2,750/wk
Off Season:
$150 - $200/night
$1,000 - $2,000/wk
Osterville
ID 29488
3 BR
1 ½ bath
Sleeps 8
3 Br, Remodeled, Central Ac, Beach Pass Wr#134586
3 Br, Remodeled, Central Ac, Beach Pass Wr#134586
Distance to beach: over 1 mile to Dowses Beach
Summer:
$1,675 - $2,200/wk
Off Season:
$250 - $275/night
$1,400/wk
Osterville
ID 5286
3 BR
2 baths
Sleeps 8
Osterville Escape
Osterville Escape
Distance to beach: 4/10 mile to ponds, less than 2 miles to Dowses
1 review read review
Summer:
$1,700/wk
Off Season:
$175 - $225/night
$1,200 - $1,700/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: Joshua's Pond (400 ft.) and Dowses Beach (1 mile)
19 reviews read reviews
OWNER SPECIAL:
The new Mass. lodging tax takes effect on July 1st, so save some money by renting in spring!
Summer:
$2,000 - $2,490/wk
$6,000 - $10,300/mo
Off Season:
$230/night
$1,440 - $2,490/wk
$3,100 - $7,400/mo
Osterville
ID 19650
3 BR
2 baths
Sleeps 7
Spacious Family Getaway Home
Spacious Family Getaway Home
Distance to beach: 2 miles Dowses Beach
9 reviews read reviews
Summer:
$1,750/wk
Osterville
ID 31739
2 BR
2 baths
Sleeps 7
Contemporary Osterville ranch with Central A/C.
Contemporary Osterville ranch with Central A/C.
Distance to beach: 3 miles to Craigville Beach
Summer:
$2,000/wk
Off Season:
$200 - $300/night
$1,000 - $1,500/wk

Osterville vacation rentals that sleep 6

Osterville
ID 19974
3 BR
2 ½ baths
Sleeps 6
Walk to Quaint Osterville Village!
Walk to Quaint Osterville Village!
Distance to beach: 1/2 mile to Dowse's Beach
3 reviews read reviews
Summer:
$2,700/wk
Off Season:
$2,500 - $2,700/wk