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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.

19 properties
Osterville Guide

Osterville vacation rentals that sleep 12
Osterville
ID 37643
5 BR
4 baths
Sleeps 12
Large 5BD, 4BTH Waterfront Home with Deep Water Dock
Large 5BD, 4BTH Waterfront Home with Deep Water Dock
Distance to beach: Waterfront with Deep Water Dock
Off Season:
 $7,070 - $8,070/wk

Osterville vacation rentals that sleep 10
Osterville/ Centerville Line
ID 39006
5 BR
3 baths
Sleeps 10
* New 2024* Luxury Coastal Retreat w/ Heated Saltwater Pool
* New 2024* Luxury Coastal Retreat w/ Heated Saltwater Pool
Distance to beach: 1.4 mi to Joshua Pond and 2.4 mi Dowses
Off Season:
 $1,143 - $1,600/night
 $7,000 - $12,500/wk
2
Osterville
ID 35972
4 BR
2 ½ baths
Sleeps 10
Osterville retreat - now booking in 2026!
Osterville retreat - now booking in 2026!
Distance to beach: 2.4 mi to Dowses
4.910 reviews
Summer:
 $3,950/wk
Off Season:
 $2,500 - $3,950/wk
 $3,000 - $3,950/mo
2
Osterville
ID 37082
4 BR
3 ½ baths
Sleeps 10
Seasons by the Sea-newly renovated home sleeps up to 10
Seasons by the Sea-newly renovated home sleeps up to 10
Distance to beach: 1/2 mi to Joshua Pond and 2 mi to Dowses
5.04 reviews
Summer:
 $8,750/wk
Off Season:
 $750/night
 $5,250 - $8,750/wk
4
Osterville
ID 39748
4 BR
3 baths
Sleeps 10
Quintessential Home Walk to Joshua's Pond Sleeps 10
Quintessential Home Walk to Joshua's Pond Sleeps 10
Distance to beach: 0.3 mi to Joshua Pond and 2 mi to Dowses
Summer:
 $8,000/wk
Off Season:
 $495 - $849/night
 $3,465 - $6,000/wk
5

Osterville vacation rentals that sleep 9
Osterville
ID 38500
4 BR
3 ½ baths
Sleeps 9
Private Oasis: Elegant Comfort & Free Beach Pass
Private Oasis: Elegant Comfort & Free Beach Pass
Distance to beach: 2.9 mi to Dowses and 4.9 mi to Craigville Beach
5.01 review
Off Season:
 $400/night
 $2,500 - $5,500/wk
3
Osterville - Barnstable
ID 36837
3 BR
2 baths
Sleeps 9
Cape Escape with Beach pass- Last minute booking savings
Cape Escape with Beach pass- Last minute booking savings
Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses
5.08 reviews
Summer:
 $2,800 - $3,300/wk
 $13,000 - $14,000/mo
Off Season:
 $500 - $589/night
 $1,500 - $2,800/wk
 $6,000 - $7,500/mo
2

Osterville vacation rentals that sleep 8
Osterville
ID 40209
4 BR
2 ½ baths
Sleeps 8
Welcome to the Birds Nest RPMS032
Welcome to the Birds Nest RPMS032
Distance to beach: 1.1 mi to Joshua Pond
Off Season:
 $6,300/wk
Osterville
ID 40223
4 BR
4 ½ baths
Sleeps 8
Heated pool, close to beach. RPMS125
Heated pool, close to beach. RPMS125
Distance to beach: 1.6 mi to Dowses
1 review
Off Season:
 $13,006/wk
Osterville
ID 37412
3 BR
2 baths
Sleeps 8
Pristine Family Vacation Home/Beach Pass Included
Pristine Family Vacation Home/Beach Pass Included
Distance to beach: 1.8 mi to Joshua Pond and 3.2 Dowses
5.08 reviews
Off Season:
 $315 - $320/night
 $2,200 - $2,400/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
5.04 reviews
3

Osterville vacation rentals that sleep 7
Osterville
ID 23526
3 BR
2 baths
Sleeps 7
Charming Garden and New Patio. Walk to Main St. and a Swim!
Charming Garden and New Patio. Walk to Main St. and a Swim!
Distance to beach: 3/10 mile to Joshua Pond and 1 mile to Dowses
5.036 reviews
Summer:
 $3,490/wk
Off Season:
 $2,060 - $3,200/wk
6
Osterville Centerville Barnsta
ID 19650
3 BR
2 baths
Sleeps 7
Escape to our Family Getaway;Barnstable Beach Pass included
Escape to our Family Getaway;Barnstable Beach Pass included
Distance to beach: 2 1/2 Craigville Beach and 2 miles Dowses Beach
5.014 reviews
Summer:
 $2,400 - $2,500/wk
7
Osterville
ID 40190
3 BR
2 ½ baths
Sleeps 7
Oasis in Osterville
Oasis in Osterville
Distance to beach: 1.5 mi to Hamblin Pond and 3.2 mi Dowses
Summer:
 $400/night
 $2,800/wk
Off Season:
 $400/night
 $2,000/wk

Osterville vacation rentals that sleep 6
Osterville
ID 39880
3 BR
2 baths
Sleeps 6
Fall Fun - Osterville Retreat with Beach Pass
Fall Fun - Osterville Retreat with Beach Pass
Distance to beach: 1.3 mi to Joshua Pond and 2 miles Dowses
5.01 review
Summer:
 $2,950/wk
 $10,500 - $11,000/mo
Off Season:
 $300/night
 $2,000 - $2,275/wk
 $3,500 - $8,500/mo
3
Osterville
ID 36955
3 BR
2 baths
Sleeps 6
Spacious Home/Walk to Town/Beach Pass & Kayaks Included
Spacious Home/Walk to Town/Beach Pass & Kayaks Included
Distance to beach: 1.0 mi to Dowses and 1.0 mi to Craigville Beach
Off Season:
 $3,000 - $6,000/wk
2

Osterville vacation rentals that sleep 5
Osterville
ID 39104
2 BR
2 baths
Sleeps 5
Osterville, Walk to Village. Bike to beach or use Beach Pass
Osterville, Walk to Village. Bike to beach or use Beach Pass
Distance to beach: 1.2 miles to Joshua Pond and 1.2 miles to Dowses
Summer:
 $3,000/wk
 $12,000/mo
Off Season:
 $2,500 - $2,900/wk
 $7,000 - $12,000/mo

Osterville vacation rentals that sleep 4
Osterville
ID 40214
2 BR
1 bath
Sleeps 4
Charming cottage steps to Osterville village. Near Dowses b
Charming cottage steps to Osterville village. Near Dowses b
Distance to beach: 0.7 mi to Joshua Pond
Summer:
 $2,303/wk
Off Season:
 $1,904 - $2,303/wk
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
5.07 reviews
Summer:
 $2,500/wk
Off Season:
 $1,000/night
 $1,750 - $2,500/wk
 $2,500 - $4,000/mo