Osterville
2 guests

Adults:

2

Children:

0

Child’s age:

Osterville

Nov 09 - Nov 10 ·
2 guests

Osterville Vacation Rentals

Osterville
2 guests

Adults:

2

Children:

0

Child’s age:

Over 10 stays assessed to highlight the standout picks

Navigation

1. Osterville Odyssey

2. Osterville Gem Steps To Main St! Relax Fireside

3. Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass

4. Walk To Shops & Dining: Cozy Osterville Cottage

Cheap Osterville Vacation Rentals

5. Osterville Retreat - A/C, Wifi Pet-Friendly

6. Wisteria Haven

7. On Cape Time - Family Friendly Relaxing Escape

Pet Friendly Vacation Rentals Osterville

8. 2 Mi To Dowses Beach! Couples Haven In Osterville

9. Cape Cod Retreat, Osterville Beach Pass

10. Olde Millie - Ost - Omr34

Best Osterville Vacation Rentals

Osterville Odyssey Osterville Odyssey

Osterville Odyssey

6 Fir Ln
2.0 km (1.2 mi) from city center
141
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Nestled a 17-minute walk from Skunknett River Wildlife Sanctuary, Osterville Odyssey villa entices guests to explore various tourist destinations nearby. The 3-bedroom holiday home hosts up to 6 guests and provides them with private parking.

9
1 reviews
~ US$562 / night

Osterville Odyssey

2.0 km (1.2 mi) from city center
141
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Osterville Odyssey

Nestled a 17-minute walk from Skunknett River Wildlife Sanctuary, Osterville Odyssey villa entices guests to explore various tourist destinations nearby. The 3-bedroom holiday home hosts up to 6 guests and provides them with private parking.

9
1 reviews
From US$ 562 / night
Osterville Gem Steps To Main St! Relax Fireside Osterville Gem Steps To Main St! Relax Fireside

Osterville Gem Steps To Main St! Relax Fireside

933 Main St Unit B
0.2 km (0.1 mi) from city center
47
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Heating
  • Terrace
  • Patio

Located just 0.7 km from united methodist church, the 2-bedroom Osterville Gem Steps To Main St! Relax Fireside villa provides access to various tourist attractions in the vicinity. This Osterville holiday home is suitable for up to 4 guests and features private parking.

10
1 reviews

Osterville Gem Steps To Main St! Relax Fireside

0.2 km (0.1 mi) from city center
47
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Heating
  • Terrace
  • Patio

Osterville Gem Steps To Main St! Relax Fireside

Located just 0.7 km from united methodist church, the 2-bedroom Osterville Gem Steps To Main St! Relax Fireside villa provides access to various tourist attractions in the vicinity. This Osterville holiday home is suitable for up to 4 guests and features private parking.

10
1 reviews
  • Private beach
Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass

Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass

127 Rebecca Ln Second Floor
3.0 km (1.9 mi) from city center
74
  • Cookware/ Kitchen utensils
  • Free parking
  • Housekeeping
  • Air conditioning
  • Live entertainment
  • Sun loungers

To enjoy your vacation in Osterville, stay at the spacious 74 m² Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass Osterville apartment, which is approximately a 10-minute ride from the Large Craigville Public Beach and within a 4-km distance of Dowses Beach. Wi-Fi and a private parking lot are also available at the 2-bedroom apartment.

An assortment of activities, such as mini golf, is available near the apartment.

10
1 reviews

Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass

3.0 km (1.9 mi) from city center
74
  • Cookware/ Kitchen utensils
  • Free parking
  • Housekeeping
  • Air conditioning
  • Live entertainment
  • Sun loungers

Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass

To enjoy your vacation in Osterville, stay at the spacious 74 m² Quiet 2Br Retreat - In-Unit Wd - Free Beach Pass Osterville apartment, which is approximately a 10-minute ride from the Large Craigville Public Beach and within a 4-km distance of Dowses Beach. Wi-Fi and a private parking lot are also available at the 2-bedroom apartment.

An assortment of activities, such as mini golf, is available near the apartment.

10
1 reviews

Cheap Osterville Vacation Rentals

  • Top location
Walk To Shops & Dining: Cozy Osterville Cottage Walk To Shops & Dining: Cozy Osterville Cottage

Walk To Shops & Dining: Cozy Osterville Cottage

933 Main St Unit A
0.2 km (0.1 mi) from city center
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Terrace
  • Patio

Nestled just a 10-minute walk from united methodist church, Walk To Shops & Dining: Cozy Osterville Cottage entices guests to explore various tourist destinations nearby. The 2-bedroom holiday home hosts up to 5 guests and provides them with private car parking.

8
1 reviews

Walk To Shops & Dining: Cozy Osterville Cottage

0.2 km (0.1 mi) from city center
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Terrace
  • Patio

Walk To Shops & Dining: Cozy Osterville Cottage

Nestled just a 10-minute walk from united methodist church, Walk To Shops & Dining: Cozy Osterville Cottage entices guests to explore various tourist destinations nearby. The 2-bedroom holiday home hosts up to 5 guests and provides them with private car parking.

8
1 reviews
  • Great deal
  • Beach access
Osterville Retreat - A/C, Wifi Pet-Friendly Osterville Retreat - A/C, Wifi Pet-Friendly

Osterville Retreat - A/C, Wifi Pet-Friendly

55 Wianno Circle
1.1 km (0.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Fitness centre

Osterville Retreat - A/C, Wifi Pet-Friendly villa is located around 10 minutes' drive from Covell's Beach and provides fisheries for active guests. This Osterville holiday home is suitable for up to 6 guests and features a private parking lot.

Osterville Retreat - A/C, Wifi Pet-Friendly

1.1 km (0.7 mi) from city center
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Fitness centre

Osterville Retreat - A/C, Wifi Pet-Friendly

Osterville Retreat - A/C, Wifi Pet-Friendly villa is located around 10 minutes' drive from Covell's Beach and provides fisheries for active guests. This Osterville holiday home is suitable for up to 6 guests and features a private parking lot.

  • Beach access
Wisteria Haven Wisteria Haven

Wisteria Haven

45 Gunstock Road
2.4 km (1.5 mi) from city center
202
  • BBQ facilities
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Fitness centre
  • Sun loungers

The 3-bedroom Wisteria Haven Villa Osterville entices guests to enjoy fishing and is located 4.5 km from such natural sites as Grand Island.

Wisteria Haven

2.4 km (1.5 mi) from city center
202
  • BBQ facilities
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Fitness centre
  • Sun loungers

Wisteria Haven

The 3-bedroom Wisteria Haven Villa Osterville entices guests to enjoy fishing and is located 4.5 km from such natural sites as Grand Island.

Pet Friendly Vacation Rentals Osterville

  • Beach access
On Cape Time - Family Friendly Relaxing Escape On Cape Time - Family Friendly Relaxing Escape

On Cape Time - Family Friendly Relaxing Escape

65 Wianno Circle
1.1 km (0.7 mi) from city center
162
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating

Hosting up to 8 guests, On Cape Time - Family Friendly Relaxing Escape Villa Osterville is nestled in a residential area, 3.1 km from Grand Island. Guests can enjoy fisheries at this 2-bathroom villa, located 15 minutes by car from Toad Hall Classic Sports Car Museum.

On Cape Time - Family Friendly Relaxing Escape

1.1 km (0.7 mi) from city center
162
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating

On Cape Time - Family Friendly Relaxing Escape

Hosting up to 8 guests, On Cape Time - Family Friendly Relaxing Escape Villa Osterville is nestled in a residential area, 3.1 km from Grand Island. Guests can enjoy fisheries at this 2-bathroom villa, located 15 minutes by car from Toad Hall Classic Sports Car Museum.

2 Mi To Dowses Beach! Couples Haven In Osterville 2 Mi To Dowses Beach! Couples Haven In Osterville

2 Mi To Dowses Beach! Couples Haven In Osterville

240 Tower Hill Rd Cottage
0.7 km (0.4 mi) from city center
47
  • Cookware/ Kitchen utensils
  • Car park
    Charges may apply
  • Express check-in/ -out
  • Flat-screen TV
  • Ironing facilities
  • Sun loungers

2 Mi To Dowses Beach! Couples Haven In Osterville villa is nestled an 8-minute walk from Armstrong-Kelley Park and can accommodate up to 2 guests.

2 Mi To Dowses Beach! Couples Haven In Osterville

0.7 km (0.4 mi) from city center
47
  • Cookware/ Kitchen utensils
  • Car park
    Charges may apply
  • Express check-in/ -out
  • Flat-screen TV
  • Ironing facilities
  • Sun loungers

2 Mi To Dowses Beach! Couples Haven In Osterville

2 Mi To Dowses Beach! Couples Haven In Osterville villa is nestled an 8-minute walk from Armstrong-Kelley Park and can accommodate up to 2 guests.

Cape Cod Retreat, Osterville Beach Pass Cape Cod Retreat, Osterville Beach Pass

Cape Cod Retreat, Osterville Beach Pass

55 Deerfield Road
1.7 km (1.1 mi) from city center
139
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

Offering guests to unwind in a hot tub, Cape Cod Retreat, Osterville Beach Pass villa is located an 18-minute walk from Skunknett River Wildlife Sanctuary. This holiday home hosts up to 6 guests and provides them with private parking.

Cape Cod Retreat, Osterville Beach Pass

1.7 km (1.1 mi) from city center
139
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Terrace

Cape Cod Retreat, Osterville Beach Pass

Offering guests to unwind in a hot tub, Cape Cod Retreat, Osterville Beach Pass villa is located an 18-minute walk from Skunknett River Wildlife Sanctuary. This holiday home hosts up to 6 guests and provides them with private parking.

Osterville Vacation Rentals Oceanfront

Olde Millie - Ost - Omr34 Olde Millie - Ost - Omr34

Olde Millie - Ost - Omr34

34 Old Mill Road
0.7 km (0.4 mi) from city center
120
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating

Olde Millie - Ost - Omr34 Villa Osterville is nestled just a 6-minute walk from Armstrong-Kelley Park and can accommodate up to 6 guests. Located 2.4 km from Skunknett River Wildlife Sanctuary, this 2-bathroom villa provides Wi-Fi and a private parking lot.

Cycling and fisheries are available.

Olde Millie - Ost - Omr34

0.7 km (0.4 mi) from city center
120
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating

Olde Millie - Ost - Omr34

Olde Millie - Ost - Omr34 Villa Osterville is nestled just a 6-minute walk from Armstrong-Kelley Park and can accommodate up to 6 guests. Located 2.4 km from Skunknett River Wildlife Sanctuary, this 2-bathroom villa provides Wi-Fi and a private parking lot.

Cycling and fisheries are available.

Vacation rentals near Osterville

  • Guest favorite
  • Beach access
Capricorn House Capricorn House

Capricorn House

79 Seaview Avenue
24.0 km (14.9 mi) from Osterville
  • Heating
  • Terrace

The historic East Chop Lighthouse is around a 25-minute walk from the 7-room Capricorn House Apartment Oak Bluffs, while Ocean Park is situated nearby.

9
171 reviews
~ US$225 / night

Capricorn House

24.0 km (14.9 mi) from Osterville
  • Heating
  • Terrace

Capricorn House

The historic East Chop Lighthouse is around a 25-minute walk from the 7-room Capricorn House Apartment Oak Bluffs, while Ocean Park is situated nearby.

9
171 reviews
From US$ 225 / night
Portside Tavern Portside Tavern

Portside Tavern

72 North Street
8.9 km (5.5 mi) from Osterville
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Bar/ Lounge area
  • Sun terrace

Located 3.5 km from Englewood Beach, the 5-room Portside Tavern Hyannis apartment gives access to a number of tourist attractions in the area. Wi-Fi is provided for both business and leisure activities.

9.1
57 reviews
~ US$200 / night

Portside Tavern

8.9 km (5.5 mi) from Osterville
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Bar/ Lounge area
  • Sun terrace

Portside Tavern

Located 3.5 km from Englewood Beach, the 5-room Portside Tavern Hyannis apartment gives access to a number of tourist attractions in the area. Wi-Fi is provided for both business and leisure activities.

9.1
57 reviews
From US$ 200 / night

Osterville Vacation Rentals with Private Pool

Renovated & Sophisticated Home Near Beach & Shops! Renovated & Sophisticated Home Near Beach & Shops!

Renovated & Sophisticated Home Near Beach & Shops!

31 General Patton Drive
8.3 km (5.2 mi) from Osterville
160
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf centre
  • Terrace

Offering access to entertainment venues such as the community-focused Cape Cod Beer Brewery, situated approximately a 10-minute drive away, the 3-bedroom Renovated & Sophisticated Home Near Beach & Shops! Barnstable can host up to 8 guests. Providing guests with Wi-Fi and parking, the Barnstable villa is 3.5 km from Colonial Acres Beach.

A Jacuzzi are also offered for ultimate relaxation.

9.5
46 reviews
~ US$227 / night

Renovated & Sophisticated Home Near Beach & Shops!

8.3 km (5.2 mi) from Osterville
160
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf centre
  • Terrace

Renovated & Sophisticated Home Near Beach & Shops!

Offering access to entertainment venues such as the community-focused Cape Cod Beer Brewery, situated approximately a 10-minute drive away, the 3-bedroom Renovated & Sophisticated Home Near Beach & Shops! Barnstable can host up to 8 guests. Providing guests with Wi-Fi and parking, the Barnstable villa is 3.5 km from Colonial Acres Beach.

A Jacuzzi are also offered for ultimate relaxation.

9.5
46 reviews
From US$ 227 / night
  • Best-rated
Thomas Sea Suites At Harbourtown Thomas Sea Suites At Harbourtown

Thomas Sea Suites At Harbourtown

150 Water Street Floor 2
43.7 km (27.2 mi) from Osterville
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Entertainment

Thomas Sea Suites At Harbourtown Plymouth overlooks the sea and is situated 5 minutes' walk from Village Landing Marketplace Shopping Center. Staying in this apartment, set in proximity to Mayflower II, guests can avail themselves of a clothes dryer.

9.2
110 reviews
~ US$402 / night

Thomas Sea Suites At Harbourtown

43.7 km (27.2 mi) from Osterville
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Entertainment

Thomas Sea Suites At Harbourtown

Thomas Sea Suites At Harbourtown Plymouth overlooks the sea and is situated 5 minutes' walk from Village Landing Marketplace Shopping Center. Staying in this apartment, set in proximity to Mayflower II, guests can avail themselves of a clothes dryer.

9.2
110 reviews
From US$ 402 / night
Epic Downtown Newport Location W Parking Epic Downtown Newport Location W Parking

Epic Downtown Newport Location W Parking

10 Fair St
78.8 km (49.0 mi) from Osterville
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Terrace

The 5-room Epic Downtown Newport Location W Parking Villa offers proximity to such city sites as Queen Anne Square Park, located just 6 minutes' walk away.

9.2
72 reviews
~ US$382 / night

Epic Downtown Newport Location W Parking

78.8 km (49.0 mi) from Osterville
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Terrace

Epic Downtown Newport Location W Parking

The 5-room Epic Downtown Newport Location W Parking Villa offers proximity to such city sites as Queen Anne Square Park, located just 6 minutes' walk away.

9.2
72 reviews
From US$ 382 / night

Are you in a hurry?

Here is a quick list of Vacation Rentals in Osterville, selected based on their rating

Name of hotel Accommodation Rating Price, $
Osterville Odyssey

9.0 / 10

(1 Reviews)

From 562$
Capricorn House

9.0 / 10

(171 Reviews)

From 225$
Portside Tavern

9.1 / 10

(57 Reviews)

From 200$
Renovated & Sophisticated Home Near Beach & Shops!

9.5 / 10

(46 Reviews)

From 227$
Thomas Sea Suites At Harbourtown

9.2 / 10

(110 Reviews)

From 402$

Frequently Asked Questions

Which Osterville vacation rentals offer a beach proximity?

The Osterville Gem is steps away from Osterville Main Street and a short walk to Dowses Beach, making it perfect for beach lovers. Couples can also enjoy the Couples Haven, only 2 miles from Dowses Beach, ensuring quick access to the water.

Tip:

Visit Dowses Beach early in the morning to find free parking and enjoy quieter spots on the sand.

What vacation rentals in Osterville have pet-friendly options?

Osterville Retreat offers air conditioning, Wi-Fi, and is pet-friendly, making it ideal for travelers with furry friends. Additionally, Wisteria Haven provides a cozy atmosphere for you and your pet.

Tip:

Choose accommodations that specify 'pet-friendly' to avoid any extra fees or restrictions when traveling with pets.

Which Osterville rentals are suitable for families?

On Cape Time is designed for families looking for a relaxing escape with family-friendly amenities. Walk To Shops & Dining: Cozy Osterville Cottage is great for families wanting to be near dining and shopping options.

Tip:

Reserve family accommodations close to popular attractions, such as Osterville Main Street, to minimize travel time for kids.

Are there vacation rentals in Osterville with kitchens?

Capricorn House and Renovated & Sophisticated Home Near Beach & Shops! include kitchens, making it easier for families to prepare meals. This can help save on dining costs during your stay.

Tip:

Plan grocery shopping for weekdays at local markets to find fresh produce and lower prices compared to weekends.

Which rentals in Osterville are ideal for special occasions?

Osterville Odyssey provides elegant surroundings for special moments, while the Osterville Gem offers a cozy vibe for romantic getaways. Both have comfortable amenities for memorable stays.

Tip:

Plan surprise dinners at nearby restaurants like the Portside Tavern to celebrate occasions during your stay.

What vacation rentals in Osterville offer outdoor spaces?

Many rentals, such as the Quiet 2Br Retreat, provide outdoor areas for relaxation. Guests can enjoy fresh air and outdoor dining options in their private space.

Tip:

Enjoy outdoor activities during the mild evenings, ideally after 5 PM, to take advantage of cooler temperatures and beautiful sunsets.

Which Osterville rentals are cost-effective for a longer stay?

Osterville Retreat offers flexible rates for extended stays, and Walk To Shops & Dining: Cozy Osterville Cottage is budget-friendly for families requiring longer accommodations.

Tip:

Consider booking during off-peak seasons, like early spring, for better rates on extended stays.

What unique events can I attend in Osterville during my visit?

During the summer, the Osterville Village Library hosts summer activities, including story times and craft fairs. These events are perfect for families looking to engage with the community.

Tip:

Plan your visit for July to enjoy summer festivals, where you can experience local arts and crafts along with delicious food.

How can I get to Osterville from the nearest airport?

You can reach Osterville from Barnstable Municipal Airport by taxi, which takes about 15-20 minutes. Alternatively, rideshare apps are also available for convenience.

Tip:

Book rides in advance, especially on weekends, to avoid long wait times at the airport.

What is the best way to get around Osterville to explore attractions?

Osterville is best explored by car, with easy access to local attractions via Main Street. Biking is also a popular choice for shorter distances.

Tip:

Consider taking a bike rental along Main Street for an enjoyable tour while stopping at various shops and local eateries.

Location