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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.

Osterville Travel Guide

25 Vacation Properties in Osterville

Sleeps

A fee-based feature highlighting availability within the next 4 weeks.

Osterville vacation rentals that sleep 14

Osterville

ID 37315

7 BR

5 ½ baths

Sleeps 14

Impressive Osterville Residence - w/Guest House

Distance to beach:

Summer:
$17,000/wk

Osterville vacation rentals that sleep 12

Osterville

ID 38649

6 BR

8 baths

Sleeps 12

*New 2024* Osterville Seaside Estate

Distance to beach: 0.3 mi to Dowses

Summer:
$26,050 - $26,297/wk

Osterville

ID 36579

5 BR

4 ½ baths

Sleeps 12

Wianno Ave Home With Pool

Distance to beach: 0.6 mi to Dowses and Sea View Beach

Summer:
$25,000/wk

Off Season:
$25,000/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

Distance to beach: 1.4 mi to Joshua Pond and 2.4 mi Dowses

LAST MINUTE ALERT 9/28 - 10/5

OWNER SPECIAL:

Fall Special- book for 7 nights for $5000. You save $2500 from the regular rate of $7500 per week.

Off Season:
$1,072 - $1,500/night
$5,000 - $8,500/wk

Osterville

ID 35972

4 BR

2 ½ baths

Sleeps 10

One summer week left!!! 8/23-Osterville retreat

Distance to beach: 2.4 mi to Dowses

9 reviews read reviews

Summer:
$3,950/wk

Off Season:
$350 - $450/night
$3,000 - $4,950/wk
$3,000 - $4,000/mo

Osterville

ID 37082

4 BR

3 ½ baths

Sleeps 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

4 reviews read reviews

OWNER SPECIAL:

Reduced minimum stay in off Season with new nightly rate. Inquire for more info.

Summer:
$7,500 - $8,750/wk

Off Season:
$750 - $1,000/night
$5,250 - $8,750/wk

Osterville

ID 37549

4 BR

2 baths

Sleeps 10

Spacious Home, Quiet Neighborhood, Great for Families

Distance to beach: .8 miles Joshua Pond and 2.1 mi to Dowses

12 reviews read reviews

OWNER SPECIAL:

Home is available to rent short or long-term during the off-season. Reach out for more Info!

Summer:
$3,500/wk

Off Season:
$400 - $500/night
$2,800 - $3,500/wk

Osterville

ID 37314

4 BR

4 ½ baths

Sleeps 10

Sea View Ave - New Construction - Pool Hot Tub Tennis Court

Distance to beach: 0.25 mi to Dowses

Summer:
$35,000/wk

Off Season:
$35,000/wk

Osterville vacation rentals that sleep 9

Osterville

ID 38500

4 BR

3 ½ baths

Sleeps 9

Walking Distance to French Bakery/Beach Pass Provided

Distance to beach: 2.9 mi to Dowses Beach; 4.9 mi to Craigville Beach

Summer:
$4,400 - $5,500/wk

Off Season:
$500 - $600/night
$2,000 - $4,400/wk

Osterville - Barnstable

ID 36837

3 BR

2 baths

Sleeps 9

Labor Day Special with Beach Pass

Distance to beach: 1/2 mile Joshua Pond and 2 miles Dowses

5 reviews read reviews

Summer:
$2,500 - $3,200/wk
$10,000 - $14,000/mo

Off Season:
$300 - $350/night
$1,500 - $2,500/wk
$4,000 - $8,000/mo

Osterville vacation rentals that sleep 8

Osterville

ID 35895

3 BR

2 ½ baths

Sleeps 8

Osterville- New renovation, central AC, beach pass included

Distance to beach: 3/10 mi to Joshua Pond

13 reviews read reviews

Summer:
$4,600/wk

Off Season:
$300 - $500/night
$2,100 - $2,700/wk

Osterville

ID 37412

3 BR

2 baths

Sleeps 8

Pristine Family Vacation Home/Beach Pass Included

Distance to beach: 1.8 mi to Joshua Pond and 3.2 Dowses

6 reviews read reviews

Summer:
$2,400 - $3,200/wk

Off Season:
$315 - $370/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

Distance to beach: 1.2 mi to Dowses and 3.5 mi Craigville Beach

4 reviews read reviews

Summer:
$2,100 - $2,500/wk

Off Season:
$2,500/wk

Osterville

ID 37316

3 BR

1 ½ bath

Sleeps 8

Osterville Village - Large Yard & Outdoor Patio

Distance to beach: 1 mile to Dowses

Summer:
$7,000/wk

Osterville vacation rentals that sleep 7

Osterville Barnstable

ID 19650

3 BR

2 baths

Sleeps 7

Spacious Family Getaway Home

Distance to beach: 2 1/2 Craigville Beach and 2 miles Dowses Beach

13 reviews read reviews

Summer:
$2,250 - $2,300/wk
$10,600/mo

Off Season:
$295 - $325/night
$2,000 - $2,200/wk

Osterville

ID 23526

3 BR

2 baths

Sleeps 7

Delightful Osterville Haven. Walk to Main St. and a Swim!

Distance to beach: 3/10 mile to Joshua Pond and 1 mile to Dowses

34 reviews read reviews

Summer:
$2,650 - $3,300/wk

Off Season:
$1,780 - $2,440/wk

Osterville vacation rentals that sleep 6

Osterville Woods

ID 35272

3 BR

3 baths

Sleeps 6

Osterville Great Family Rental!

Distance to beach: 1.5 Joshua Pond and 3.0 Dowses

Summer:
$2,600 - $3,200/wk

Off Season:
$225/night
$2,000 - $2,500/wk
$2,500 - $3,000/mo

Carriage House

ID 38342

3 BR

2 baths

Sleeps 6

Carriage House - Oceanfront - Overlooking Dowses Beach

Distance to beach: 5/10 to dowses Dowses and private beach off wooden walkway on the property

Summer:
$7,500/wk
$30,000 - $37,500/mo

Off Season:
$7,500/wk

Osterville

ID 38319

3 BR

2 baths

Sleeps 6

Dog Friendly Charmer - Convenient Location

Distance to beach: 1.6 miles Joshua Pond and 3.0 miles Dowses

Off Season:
$175 - $215/night
$1,500 - $1,800/wk
$2,000/mo

Osterville

ID 38786

3 BR

2 baths

Sleeps 6

Newly Renovated Osterville Home: Beach Pass Included

Distance to beach: 1.6 mi to Joshua Pond and 1.5 mi Dowses

OWNER SPECIAL:

Price Reduction and 2025 Summer Special.

Summer:
$3,200/wk

Off Season:
$350 - $650/night
$2,500 - $3,000/wk

Osterville

ID 32374

3 BR

2 ½ baths

Sleeps 6

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:
$4,000/wk

Off Season:
$3,500 - $4,000/wk

Osterville

ID 36955

3 BR

2 baths

Sleeps 6

Spacious Home/Walk to Town/Beach Pass & Kayaks Included

Distance to beach: 1.0 mi to Dowses and 1.0 mi to Craigville Beach

Summer:
$5,000 - $6,000/wk

Off Season:
$4,000 - $5,000/wk

Osterville vacation rentals that sleep 5

Osterville Village (Wianno Ave

ID 27783

2 BR

1 bath

Sleeps 5

WINTER RENTAL in Osterville Village (also 2025 summer)

Distance to beach: .9 miles to Dowses and 3.4 miles Craigville Beach

OWNER SPECIAL:

Winter Rental $2200mo plus. Oct-June.

Summer:
$2,849/wk
$3,200/mo

Off Season:
$425/night
$1,000 - $2,849/wk
$2,200 - $3,500/mo

Osterville vacation rentals that sleep 4

Osterville

ID 34848

2 BR

1 ½ bath

Sleeps 4

Enchanting Cottage - one block to Osterville Village!

Distance to beach: 0.5 mi to Joshua Pond and 1.5 mi to Dowses

6 reviews read reviews

Off Season:
$1,500 - $2,000/wk
$2,500 - $6,000/mo

Osterville vacation rentals that sleep 3

Osterville

ID 37628

3 BR

3 ½ baths

Sleeps 3

Charming Osterville Home w/ Pool - Near Town

Distance to beach: 600 ft to Joshua Pond and 1.5 mi to Dowses

Summer:
$12,250/wk

Off Season:
$800 - $850/night
$6,000 - $9,000/wk