Minimap with link to location map
Filters
Price
Rating
Distance from Center
Rating (according to Stars)
Facilities

Check availability






Holiday homes in Osterville You’ll Love

Top-Rated Osterville Holiday homes for Every Budget and Style!

Looking for a holiday home in Osterville (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Osterville.

We found 88 Holiday-homes in Osterville and the surrounding area (within 20 miles)

Cape Cod house in Barnstable, USA

Cape Cod house

Villa in Barnstable near Osterville, Massachusetts , 122 Whitmar Road
Offering a garden, Cape Cod house features accommodations in Barnstable.
  • Parking

no reviews

from $66.00 Show details »

Stunning Walk to Water Home Dog Welcome in Mashpee, USA

Stunning Walk to Water Home Dog Welcome

Holiday home in Mashpee near Osterville, Massachusetts
Stunning Walk to Water Home Dog Welcome is located in Mashpee, just 15 miles from Sandwich Glass Museum and 15 miles from Heritage Museums & Gardens.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $85.00 Show details »

Beautiful Cape Cod home! Steps to beach! in Mashpee, USA

Beautiful Cape Cod home! Steps to beach!

Holiday home in Mashpee near Osterville, Massachusetts , 23 Naushon Road
Beautiful Cape Cod home!
  • Parking
  • Family rooms

no reviews

from $62.00 Show details »

Adorable Cape beach house.3 min walk to beach! Renovated in Mashpee, USA

Adorable Cape beach house.3 min walk to...

Holiday home in Mashpee near Osterville, Massachusetts , 3 Naushon Road
Adorable Cape beach house.3 min walk to beach!
  • Parking

no reviews

from $83.00 Show details »

Seabury Serenity in New Seabury, USA

Seabury Serenity

Holiday home in New Seabury near Osterville, Massachusetts
Seabury Serenity is located in New Seabury, just 15 miles from Heritage Museums & Gardens and 2.9 miles from South Cape Beach State Park.
  • Parking

Fabulous 2 Reviews 9.0

from $314.13 Show details »

Summersea in Mashpee, USA

Summersea

Holiday home in Mashpee near Osterville, Massachusetts
Summersea offers accommodations in Mashpee, 14 miles from Heritage Museums & Gardens and 3.3 miles from South Cape Beach State Park.
  • Parking

Fabulous 8 Reviews 8.6

from $269.82 Show details »

Cape Castle in Mashpee, USA

Cape Castle

Holiday home in Mashpee near Osterville, Massachusetts
Cape Castle is located in Mashpee, just 12 miles from Heritage Museums & Gardens and 30 miles from Plimoth Plantation.
  • Parking
  • Sauna
  • Outdoor pool
  • Electric vehicle charging station
  • Swimming pool

Exceptional 1 Reviews 10.0

from $1.072.68 Show details »

Cape Escape - Autumn Golfing & Walk to The Bay! in Mashpee, USA

Cape Escape - Autumn Golfing & Walk to T...

Holiday home in Mashpee near Osterville, Massachusetts , 39 Hawthorne Street
Cape Escape - Autumn Golfing & Walk to The Bay! is located in Mashpee, just 1.5 miles from Ropes Beach and 1.7 miles from Loop Beach.
  • Parking
  • Pets allowed

Good 2 Reviews 7.0

from $69.00 Show details »

The Cape House in Cotuit, USA

The Cape House

Holiday home in Cotuit near Osterville, Massachusetts
The Cape House offers accommodations in Cotuit, 28 miles from Plimoth Plantation and 9 miles from South Cape Beach State Park.
  • Parking
  • Pets allowed

Superb 7 Reviews 9.2

from $291.33 Show details »

4BR Mashpee Retreat with fireplace in Mashpee, USA

4BR Mashpee Retreat with fireplace

Holiday home in Mashpee near Osterville, Massachusetts , 17 Payamps Rd
4BR Mashpee Retreat with fireplace offers accommodations in Mashpee, 11 miles from Heritage Museums & Gardens and 27 miles from Plimoth Plantation.
  • Parking

no reviews

from $72.00 Show details »

Summer on the Cape in Mashpee, USA

Summer on the Cape

Holiday home in Mashpee near Osterville, Massachusetts
Summer on the Cape is located in Mashpee, just 10 miles from Heritage Museums & Gardens and 28 miles from Plimoth Plantation.

Very good 1 Reviews 8.0

from $429.94 Show details »

Hyannis Port Home with BBQ and Views Half Mi to Beach in Hyannis Port, USA

Hyannis Port Home with BBQ and Views Hal...

Holiday home in Hyannis Port near Osterville, Massachusetts
Hyannis Port Home with BBQ and Views Half Mi to Beach is located in Hyannis Port, just 16 miles from Sandwich Glass Museum and 16 miles from Heritage ...
  • Parking
  • Spa and wellness centre

Poor 1 Reviews 3.0

from $1.528.29 Show details »

77 Linden Lane Osterville Cape Cod - - Afterdune Delight in Osterville, USA

77 Linden Lane Osterville Cape Cod - - A...

Holiday home in Osterville, Massachusetts , 77 Linden Lane
77 Linden Lane Osterville Cape Cod - - Afterdune Delight offers accommodations in Osterville, 1.4 miles from Dowses Beach and 1.6 miles from Long Beac...
  • Parking
  • Pets allowed

Pleasant 1 Reviews 6.0

from $81.00 Show details »

Osterville Village Beauty in Osterville, USA

Osterville Village Beauty

Holiday home in Osterville, Massachusetts , 42 Pond Street
Featuring a garden, Osterville Village Beauty provides accommodations in Osterville.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $65.00 Show details »

Kalmus Park Retreat in Hyannis, USA

Kalmus Park Retreat

Holiday home in Hyannis near Osterville, Massachusetts
Kalmus Park Retreat is located in Hyannis, just 1.5 miles from Bay View Beach and 16 miles from Sandwich Glass Museum.
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $1.242.73 Show details »

Coastal Retreat in Centerville, USA

Coastal Retreat

Holiday home in Centerville near Osterville, Massachusetts
Coastal Retreat is located in Centerville, just 14 miles from Sandwich Glass Museum and 14 miles from Heritage Museums & Gardens.
  • Parking

no reviews

from $473.98 Show details »

Kalmus Park Hideaway in Hyannis, USA

Kalmus Park Hideaway

Holiday home in Hyannis near Osterville, Massachusetts
Kalmus Park Hideaway is located in Hyannis, just a 9-minute walk from Veterans Park beach and 1.4 miles from Bay View Beach.
  • Parking

no reviews

from $76.00 Show details »

Perfect vacation getaway! in Barnstable, USA

Perfect vacation getaway!

Holiday home in Barnstable near Osterville, Massachusetts , 36 Ipswich Circle
Perfect vacation getaway! offers accommodations in Barnstable, a 15-minute walk from Long Beach and 0.9 miles from Craigville Beach.
  • Parking
  • Family rooms

Fabulous 2 Reviews 9.0

from $55.00 Show details »

Ospreys Nest in West Hyannisport, USA

Ospreys Nest

Holiday home in West Hyannisport near Osterville, Massachusetts
Ospreys Nest offers accommodations in West Hyannisport, 29 miles from Nauset Lighthouse.
  • Parking

Exceptional 2 Reviews 9.5

from $241.00 Show details »

Cape Cod Retreat Patio, Walk to Craigville Beach in Centerville, USA

Cape Cod Retreat Patio, Walk to Craigvil...

Holiday home in Centerville near Osterville, Massachusetts
The property is around 14 miles from Sandwich Glass Museum, 14 miles from Heritage Museums & Gardens, and 30 miles from Nauset Lighthouse.
  • Parking
  • Spa and wellness centre
  • Swimming pool
  • Swimming Pool

no reviews

from $246.89 Show details »

Modern Cape Cod Cottage Walk to Craigville Beach in Centerville, USA

Modern Cape Cod Cottage Walk to Craigvil...

Holiday home in Centerville near Osterville, Massachusetts
Modern Cape Cod Cottage Walk to Craigville Beach offers accommodations in Centerville, 14 miles from Sandwich Glass Museum and 14 miles from Heritage ...
  • Parking
  • Spa and wellness centre
  • Swimming pool
  • Swimming Pool

Superb 6 Reviews 9.4

from $238.87 Show details »

Wharf Side Hideout in Hyannis, USA

Wharf Side Hideout

Holiday home in Hyannis near Osterville, Massachusetts
Wharf Side Hideout offers accommodations in Hyannis, 1.5 miles from Bay View Beach and 16 miles from Sandwich Glass Museum.
  • Parking

Passable 1 Reviews 5.0

from $60.00 Show details »

Walk to Joshua Pond Beach & Downtown in Barnstable, USA

Walk to Joshua Pond Beach & Downtown

Holiday home in Barnstable near Osterville, Massachusetts
Walk to Joshua Pond Beach & Downtown offers accommodations in Barnstable, 13 miles from Sandwich Glass Museum and 13 miles from Heritage Museums & Gar...
  • Parking

no reviews

from $64.00 Show details »

Charming Hyannis Home with Deck Walk to Beach! in Hyannis, USA

Charming Hyannis Home with Deck Walk to...

Holiday home in Hyannis near Osterville, Massachusetts
Just a 14-minute walk from Veterans Park beach and 0.9 miles from Kalmus Park Beach, Charming Hyannis Home with Deck Walk to Beach! features accommoda...
  • Parking
  • Fitness centre
  • Spa and wellness centre

Very good 2 Reviews 8.5

from $485.43 Show details »

161 Bay Lane Centerville Cape Cod - Bay Breeze in Centerville, USA

161 Bay Lane Centerville Cape Cod - Bay...

Holiday home in Centerville near Osterville, Massachusetts , 161 Bay Lane
161 Bay Lane Centerville Cape Cod - Bay Breeze offers accommodations in Centerville, a 10-minute walk from Craigville Beach and 0.8 miles from Long Be...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $1.697.13 Show details »

Number of Holiday homes in Osterville 88
Number of guest ratings 4
Average price per night $313.00
Lowest price per night $51,00
Highest price per night $2.427,21

Top 10 Cheapest Holiday-homes in Osterville

Discover the Cheapest Holiday-homes in Osterville – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Osterville

Check out the Most Booked Holiday-homes in Osterville – Based on Guest Popularity.

Holiday homes in Osterville (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Osterville can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Osterville for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Osterville should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com