Osterville Holiday Rentals

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Holiday Rentals in Osterville

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
9.2 out of 10, Wonderful, 28 reviews
"Beautiful house in affluent area."
Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower
Holly Tree Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, 307 reviews
"Very clean hotel "
Holly Tree Resort by VRI Americas
Cape Winds Resort by VRI Americas
3.5 star property
8.8 out of 10, Excellent, 399 reviews
"Very accommodating!"
The price is NZ$507
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Cape Winds Resort by VRI Americas
Oceanside 2 - SD335
9.8 out of 10, Exceptional, 10 reviews
"This little cottage was perfect for my wife and I. We started coming to the Cape in the Fall because the Summers are too crowded for us there. This cottage was nearly perfect for our stay. It is nestled in a small loop off of the road where there are a few cottages. Not bad in October but probably more bustling in the Summer. The only thing I didn't like was that the path down to the beach is alongside of this cottage and when coming off the beach, everyone is passing the back deck. Otherwise,...
Oceanside 2 - SD335
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, 289 reviews
"Stayed for only one night and wished it was longer. The condo was wonderful, clean and comfortable. Because we are early in June, we went off property to enjoy dinner at the Flying Bridge. The beach was wonderful, comfy chairs, soft sand. I can say you will not regret staying here. We will be back@"
The price is NZ$970
includes taxes & fees
14 July - 15 July
14 Jul - 15 Jul
The Club at New Seabury
Historic Cape home with private pool, tennis court, summer kitchen, & game barn
9.8 out of 10, Exceptional, 17 reviews
"Our group of 11 loved this property! Having separate buildings was great for some privacy. The game barn was an absolute gem. We enjoyed hanging out there and playing pool and games. The main house is beautiful annd well stocked. All of the beds were comfortable and we had plenty of towels. We could have used an extra blanket or two, but truly we had no complaints. The house was spotless, everything was comfortable and just as described. Management was helpful with the couple questions I had."
Historic Cape home with private pool, tennis court, summer kitchen, & game barn
Dog-friendly home with firepit, deck & washer/dryer - walk to Sandy Neck Beach
9.4 out of 10, Exceptional, 32 reviews
"Beautiful home. Beautiful beaches nearby. Lovely fenced yard."
Dog-friendly home with firepit, deck & washer/dryer - walk to Sandy Neck Beach
Oceanfront Cape Cod Vacation Rental: Beach Access!
9.2 out of 10, Wonderful, 47 reviews
"very nice"
Oceanfront Cape Cod Vacation Rental: Beach Access!
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
9.6 out of 10, Exceptional, 110 reviews
"It was a perfect place, the balcony by was in the right position to watch sunrise and sunsets. Condo was very clean and comfortable."
The price is NZ$1,216
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! capeoceanvista
Steps to the Ocean! Perfect Location!!!
10.0 out of 10, Exceptional, 175 reviews
"Location is great - steps from the beach, and with a view. Well appointed, comfortable."
Steps to the Ocean! Perfect Location!!!
Quaint condo near private beach access with fireplace - close to dining
9.0 out of 10, Wonderful, 41 reviews
"Very nice condo. Clean and well stocked. Just the right size for a couple. Only a few steps from the beach, which is private. Great Cape Cod location mid way down the cape. Only 20 minutes from shopping and the fish pier in Chatham and an hour from Provincetown. We would definitely stay again. The only reason it’s a 4 star and not 5 are some minor issues that are easily addressed: Needs a new mattress on the bed. Way too soft Drain in the master bath slow Most important: The door keypad is...
The price is NZ$622
includes taxes & fees
27 June - 28 June
27 Jun - 28 Jun
Quaint condo near private beach access with fireplace - close to dining
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
9.0 out of 10, Wonderful, 33 reviews
"All the things we needed: beach, comfortable place to sleep, eat and shower. Appreciated the extra beach chairs! Plenty of towels for showering. Plenty of movies and games if there’s a bad weather day - we were lucky to have none of those! We hope to return. Thanks for sharing your place!"
The price is NZ$806
includes taxes & fees
27 June - 28 June
27 Jun - 28 Jun
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
9.8 out of 10, Exceptional, 154 reviews
"Right on the beach and a great location. Small but has all you need!"
Cape Cod/Oceanfront on Nantucket Sound w/ Private Beach & Deck, Free Kayaks
Cozy beachfront cottage at Chases Ocean Grove
10.0 out of 10, Exceptional, 12 reviews
"My friend and I had a wonderful time at your cottage. My friend had not visited the Cape in a long time so it was fun for both of us to go exploring. And it was great that the cottages were right on the beach so we did not have to drive anywhere to soak up the sunshine."
Cozy beachfront cottage at Chases Ocean Grove
Cape Cod Vacation Home Rental - Walk to Beach
10.0 out of 10, Exceptional, 7 reviews
"We loved being able to walk to cafes, restaurants and the bookstore and the proximity of the bike path meant that we didn't need our car much at all. We rode bikes to lunch spots, the beach, and to the pickleball courts. The house was tidy and had everything we needed."
Cape Cod Vacation Home Rental - Walk to Beach
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
8.8 out of 10, Excellent, 22 reviews
"Great little cozy place updated and clean close to beach"
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
9.6 out of 10, Exceptional, 5 reviews
"Thank you for a great stay! Beautiful house and location. We had a great time!"
The price is NZ$6,200
includes taxes & fees
7 July - 8 July
7 Jul - 8 Jul
Oceanfront home with private beach, large deck, & washer/dryer - dog-friendly
THE BOAT HOUSE LOFT ~ THE CAPE'S BEST WATERFRONT VALUE ~ SHORT TERM STAYS AVAIL!
9.2 out of 10, Wonderful, 86 reviews
"Larry our host was right there to greet us. Made sure we know where everything was. Very friendly.The boat loft was very quaint. Peaceful right on a nice big pond. We would go back again the next time we go to the cape. Thanks again Larry. Rhonda and Gary"
THE BOAT HOUSE LOFT ~ THE CAPE'S BEST WATERFRONT VALUE ~ SHORT TERM STAYS AVAIL!
Lovely Cape Cottage 2 bedroom with private beach and central air.
9.8 out of 10, Exceptional, 39 reviews
"This worked out perfectly for a spring getaway. Clean updated property in a great location. Thank you."
Lovely Cape Cottage 2 bedroom with private beach and central air.
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, 146 reviews
"Great place"
InnSeason Resorts Captain's Quarters
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See all available properties in Osterville
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.

Other types of properties in Osterville you may be interested in

Bayside Resort Hotel
3.0 star property
8.8 out of 10, Excellent, 1,039 reviews
"Nice place"
The price is NZ$391
includes taxes & fees
25 June - 26 June
25 Jun - 26 Jun
Bayside Resort Hotel
Cape Sands Inn
2.5 star property
8.4 out of 10, Very good, 983 reviews
"Continuo a la espere de la devolución del el pago por daños que fue debitado de mi tarjeta y no ha sido regresado. El primer día de mi estadía en el piso de arriba se escuchaba muchísimo ruido y nadie llegó a parar el ruido en toda la noche."
The price is NZ$166
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Cape Sands Inn
Summercamp
3.5 star property
9.2 out of 10, Wonderful, 657 reviews
"Very friendly helpful staff. Great location "
The price is NZ$658
includes taxes & fees
23 June - 24 June
23 Jun - 24 Jun
Summercamp
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osterville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osterville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Osterville. Seeing all the best attractions is bound to make you fall in love with Osterville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Osterville short-term rentals, that won’t be hard to do.

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?

Dog-friendly cape home with Wifi, deck, grill, fireplace, & outdoor shower: This highly rated holiday home rental in Osterville offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals are there in Osterville?

With 100 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.

Recent reviews of Osterville properties
Expedia verified reviews