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Mid Cape Cod Vacation Rentals

Osterville Vacation Rentals

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.

21 Vacation Properties in Osterville
Sleeps

Osterville vacation rentals that sleep 14

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Osterville
ID 37315
7 BR
5 ½ baths
Sleeps 14
Impressive Osterville Residence - w/Guest House
Impressive Osterville Residence - w/Guest House
Distance to beach:
Summer:
 $15,000/wk
Off Season:
 $9,500/wk

Osterville vacation rentals that sleep 12

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Osterville
ID 36579
5 BR
4 ½ baths
Sleeps 12
Wianno Ave Home With Pool
Wianno Ave Home With Pool
Distance to beach: 0.6 mi to Dowses and Sea View Beach
Summer:
 $18,000/wk
Off Season:
 $10,000 - $18,000/wk
Osterville
ID 37106
4 BR
4 baths
Sleeps 12
STARBOARD RETREAT-Spacious Osterville Home w/ Pool & Hot Tub
STARBOARD RETREAT-Spacious Osterville Home w/ Pool & Hot Tub
Distance to beach: 1.8 mi to Craigville Beach
1 review read review
Summer:
 $14,700/wk
Off Season:
 $1,200/night
 $8,400 - $14,700/wk

Osterville vacation rentals that sleep 10

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Osterville
ID 35972
4 BR
2 ½ baths
Sleeps 10
Osterville retreat. Perfect for multiple families or groups
Osterville retreat. Perfect for multiple families or groups
Distance to beach: 2.4 mi to Dowses
5 reviews read reviews
Summer:
 $5,950/wk
Off Season:
 $350 - $450/night
 $4,000 - $5,950/wk
 $3,500 - $4,500/mo
2
Osterville
ID 37082
4 BR
3 ½ baths
Sleeps 10
Newly Renovated Osterville Luxury Home Near Village
Newly Renovated Osterville Luxury Home Near Village
Distance to beach: 1/2 mi to Joshua Pond and 2 mi to Dowses
1 review read review
OWNER SPECIAL:
Want more than 7 days? Extended week available in July!
Summer:
 $7,500/wk
Off Season:
 $7,500/wk
2
Osterville
ID 37314
4 BR
4 ½ baths
Sleeps 10
Sea View Ave - New Construction - Pool Hot Tub Tennis Court
Sea View Ave - New Construction - Pool Hot Tub Tennis Court
Distance to beach: 0.25 mi to Dowses
Summer:
 $30,000/wk
Off Season:
 $22,000 - $25,000/wk

Osterville vacation rentals that sleep 9

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Osterville
ID 28091
4 BR
2 baths
Sleeps 9
Quaint Osterville Center: Beach Pass, New Beds, AC, Sleeps 9
Quaint Osterville Center: Beach Pass, New Beds, AC, Sleeps 9
Distance to beach: 4/10 mile Joshua Pond, 9/10 Dowses Beach
Summer:
 $5,000/wk
Off Season:
 $500 - $700/night
 $3,500/wk
Osterville - Barnstable
ID 36837
3 BR
2 baths
Sleeps 9
Cape Escape - Minutes to Beaches w Barnstable Beach Pass
Cape Escape - Minutes to Beaches w Barnstable Beach Pass
Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses
2 reviews read reviews
Summer:
 $3,000 - $3,200/wk
 $15,000/mo
Off Season:
 $350 - $400/night
 $2,500/wk
 $10,000 - $15,000/mo
2

Osterville vacation rentals that sleep 8

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Osterville
ID 27473
4 BR
2 baths
Sleeps 8
Close to Osterville Village!
Close to Osterville Village!
Distance to beach: 1 mile to Dowses Beach - beach sticker included
23 reviews read reviews
Summer:
 $3,600 - $3,700/wk
Off Season:
 $1,800 - $3,600/wk
4
Osterville
ID 10157
3 BR
2 baths
Sleeps 8
Osterville Three Bedroom Cape
Osterville Three Bedroom Cape
Distance to beach: 1 3/4 miles to famous Dowses private beach
Summer:
 $2,600 - $2,775/wk
Off Season:
 $250 - $350/night
 $1,750 - $2,600/wk
Osterville
ID 34432
3 BR
2 baths
Sleeps 8
Updated 3 Bedroom with AC & Great Proximity to Summer Fun
Updated 3 Bedroom with AC & Great Proximity to Summer Fun
Distance to beach: 1.2 mi to Dowses and 3.5 mi Craigville Beach
4 reviews read reviews
Summer:
 $2,500/wk
Off Season:
 $1,000/wk
3
Osterville
ID 35895
3 BR
2 ½ baths
Sleeps 8
Osterville~Newly Renovated 3BR,2.5BA w/AC near Joshua Pond
Osterville~Newly Renovated 3BR,2.5BA w/AC near Joshua Pond
Distance to beach: 3/10 mi to Joshua Pond
10 reviews read reviews
OWNER SPECIAL:
Easter Long Weekend and School Vacation price reduction in newly renovated Osterville home.
Summer:
 $4,000 - $4,500/wk
 $16,000 - $17,000/mo
Off Season:
 $255 - $530/night
 $1,800 - $3,700/wk
 $4,000 - $6,500/mo
3
Osterville
ID 36324
3 BR
2 ½ baths
Sleeps 8
Osterville Village Beauty on 6 Acres of Privacy
Osterville Village Beauty on 6 Acres of Privacy
Distance to beach: 1 mi to Joshua Pond and 1 mi to Dowses
Summer:
 $750 - $1,500/night
 $7,000 - $7,500/wk
 $30,000/mo
Off Season:
 $300 - $750/night
 $2,000 - $6,000/wk
 $3,500 - $12,000/mo
2
Osterville
ID 37316
3 BR
1 ½ bath
Sleeps 8
Osterville Village - Large Yard & Outdoor Patio
Osterville Village - Large Yard & Outdoor Patio
Distance to beach: 1 mile to Dowses
Summer:
 $6,496 - $9,496/wk
Off Season:
 $300 - $600/night
 $3,500 - $6,496/wk

Osterville vacation rentals that sleep 7

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Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Delightful, Renovated Cottage. Walk to Main St. and a Swim!
Delightful, Renovated Cottage. Walk to Main St. and a Swim!
Distance to beach: 4/10 mile to Joshua Pond and 1 mile to Dowses
29 reviews read reviews
Summer:
 $3,220/wk
Off Season:
 $1,750 - $2,620/wk
4
Osterville
ID 37214
3 BR
2 ½ baths
Sleeps 7
Aloha Osterville ~ Close to Beach and Main Street
Aloha Osterville ~ Close to Beach and Main Street
Distance to beach: 1/2 mi to Dowses
Summer:
 $2,450 - $2,975/wk
Off Season:
 $250 - $430/night
 $1,750 - $2,450/wk
3

Osterville vacation rentals that sleep 6

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Osterville
ID 32374
3 BR
2 ½ baths
Sleeps 6
Beautiful & Pristine Osterville Cape, walk to Village
Beautiful & Pristine Osterville Cape, walk to Village
Distance to beach: 1 3/10 miles to Craigville Beach and 1 6/10 miles to Dowses
Summer:
 $3,500/wk
Off Season:
 $500/night
 $3,500/wk
Osterville
ID 37313
2 BR
2 baths
Sleeps 6
The Cape Escape
The Cape Escape
Distance to beach: 2.6 mi to Craigville Beach
Summer:
 $4,850 - $5,000/wk
Off Season:
 $300 - $450/night
 $2,100 - $4,850/wk

Osterville vacation rentals that sleep 5

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Osterville
ID 37279
3 BR
1 ½ bath
Sleeps 5
Osterville Cape Cod- 3BR & Pet Friendly
Osterville Cape Cod- 3BR & Pet Friendly
Distance to beach: 3.5 miles to Craigville Beach
Summer:
 $2,205/wk
Off Season:
 $270 - $315/night
 $1,890 - $1,995/wk
Close to Town Centre
ID 35847
2 BR
2 baths
Sleeps 5
New Listing in Charming Osterville - Seasonal Rentals
New Listing in Charming Osterville - Seasonal Rentals
Distance to beach: 1.2 miles Joshua Pond and 1.5 miles Dowses
Summer:
 $2,750 - $2,950/wk
 $11,000/mo
Off Season:
 $1,500 - $3,000/wk
 $3,000 - $10,000/mo
5

Osterville vacation rentals that sleep 4

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Osterville
ID 34848
2 BR
1 ½ bath
Sleeps 4
Enchanting Cottage - one block to Osterville Village!
Enchanting Cottage - one block to Osterville Village!
Distance to beach: 0.5 mi to Joshua Pond and 1.5 mi to Dowses
4 reviews read reviews
Summer:
 $2,695 - $2,950/wk
Off Season:
 $1,500 - $2,750/wk
 $2,250 - $4,000/mo