A house by a lake with boats.

Holiday Rentals in Osterville

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Osterville holiday rentals

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Serene Haven w/ No Shared Spaces | Cape Cod

Serene Haven w/ No Shared Spaces | Cape Cod
Marston Mills
10.0 out of 10, Exceptional, (16 reviews)
"Marston Hills is a great location for getting to many great areas of Cape Cod. The house was very clean and nicely furnished. "
United States
Dana S.
The price is €399
includes taxes & fees
4 Aug - 5 Aug
Serene Haven w/ No Shared Spaces | Cape Cod

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (83 reviews)
"Great place, great location."
United States
James H.
The price is €299
includes taxes & fees
17 Aug - 18 Aug
New Seabury Cape Condo + Pool & Beach Escape

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.8 out of 10, Excellent, (6 reviews)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
United States
Meghan H.
The price is €357
includes taxes & fees
20 Jul - 21 Jul
Charming 3 bed room with magnificent views & large deck

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
Sandwich
9.6 out of 10, Exceptional, (37 reviews)
"Great location & comfortable house for exploring Cape Cod & surrounding area"
United States
Linda
The price is €533
includes taxes & fees
20 Jul - 21 Jul
5 Mi to Beach: Cape Cod Getaway w/ Grill

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
8.8 out of 10, Excellent, (19 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
The price is €331
includes taxes & fees
21 Jul - 22 Jul
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (363 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is €505
includes taxes & fees
20 Jul - 21 Jul
The Club at New Seabury

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (33 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is €1,178
includes taxes & fees
20 Jul - 21 Jul
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."
United States
Shaun G.
4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4BD/2BA. Tranquil Cape Getaway for family

4BD/2BA. Tranquil Cape Getaway for family
Barnstable
10.0 out of 10, Exceptional, (35 reviews)
"The house was perfect! "
United States
Lynn S.
4BD/2BA. Tranquil Cape Getaway for family

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
3.0 star property
Sandwich
The price is €524
includes taxes & fees
20 Jul - 21 Jul
5 Mi to Beach: Cape Cod Getaway w/ Grill

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"Cute little cottage. Clean and pull out couch was very comfy! Great stay for a small group. Perfect location near a lot of very nice beaches. Would recommend Gray’s beach for sunset, parking is free!"
United States
Jessica Y.
The price is €505
includes taxes & fees
21 Jul - 22 Jul
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (9 reviews)
"Great place"
United States
Aaron Q.
The price is €1,328
includes taxes & fees
21 Jul - 22 Jul
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Authentic, Charming Cape Cod Cottage

Authentic, Charming Cape Cod Cottage
Bass River
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and quaint cottage! Kathlene is a wonderful host and welcoming to this great little getaway. Close to the shops, restaurants, golf and activities the Cape has to offer and a short walk to the Windmill Beach. Highly recommend!"
United States
Erik S.
The price is €464
includes taxes & fees
29 Jul - 30 Jul
Authentic, Charming Cape Cod Cottage

Cape Cod Hyannis Rendezvous'

Cape Cod Hyannis Rendezvous'
Barnstable
9.8 out of 10, Exceptional, (9 reviews)
"Nice stay close to town"
United States
Daniel m.
The price is €804
includes taxes & fees
20 Jul - 21 Jul
Cape Cod Hyannis Rendezvous'

Cape Cod Loft - Near Beaches & Canal

Cape Cod Loft - Near Beaches & Canal
Bourne
10.0 out of 10, Exceptional, (21 reviews)
"Really good place to stay close to Cape Cod and enjoy to visit the place ! Beautiful neighborhood and beautiful loft! Will come back for sure"
Canada
Olivier S.
The price is €286
includes taxes & fees
12 Aug - 13 Aug
Cape Cod Loft - Near Beaches & Canal

Dream beach home on Lewis Bay with ocean views & amazing outdoor areas

Dream beach home on Lewis Bay with ocean views & amazing outdoor areas
West Yarmouth
9.2 out of 10, Wonderful, (33 reviews)
"Great stay"
United States
Christian Z.
The price is €1,096
includes taxes & fees
30 Jul - 31 Jul
Dream beach home on Lewis Bay with ocean views & amazing outdoor areas

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.4 out of 10, Exceptional, (16 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is €1,033
includes taxes & fees
22 Jul - 23 Jul
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Stay was awesome! Perfect house for family gatherings "
United States
Diana P.
The price is €1,380
includes taxes & fees
1 Aug - 2 Aug
Recently renovated 3 bedroom

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.6 out of 10, Exceptional, (49 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is €1,278
includes taxes & fees
31 Jul - 1 Aug
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Osterville Hotel Reviews

Find out more about Osterville

Everything you need to know about Osterville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osterville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osterville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osterville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osterville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osterville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osterville holiday rentals we have selected for you start as low as €450 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osterville rentals

At Expedia, we put the best Osterville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osterville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osterville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osterville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Osterville?

Yes, there are holiday rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osterville has to offer?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Osterville is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Osterville?

With 61 Expedia holiday rentals, you're guaranteed to find just the right place for your Osterville stay.

What’s there to see and do in Osterville?

Cape Cod Beaches and Dowses Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Stand Up & Paddle Cape Cod. Public Beach and Main Street are a couple of places you'll find in the wider area.

What’s a holiday rental in Osterville like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osterville. Holiday rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.