Osterville Holiday Rentals

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Our top choices for Osterville holiday rentals

Interior

Walk to Beaches & Dining: Classic Cape Cod Cottage

Walk to Beaches & Dining: Classic Cape Cod Cottage
3.0 star property
Dennis Port
The price is HK$862
HK$3,426 total
includes taxes & fees
20 Apr - 21 Apr
Walk to Beaches & Dining: Classic Cape Cod Cottage
Interior

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is HK$1,682
HK$3,735 total
includes taxes & fees
23 Apr - 24 Apr
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Exterior

Ocean View Room @ Beach Resort / Habitat *HOT TUB*

Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Cape Cod
The price is HK$783
HK$2,411 total
includes taxes & fees
3 May - 4 May
Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Sun-loungers, beach towels

Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
9.8 out of 10, Exceptional, (6 reviews)
"Great place! Great host!"
United States
Moira C.
The price is HK$1,166
HK$2,491 total
includes taxes & fees
3 May - 4 May
Make this charming, modern retreat your home away from home!!
Interior

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (52 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is HK$697
HK$1,407 total
includes taxes & fees
19 Apr - 20 Apr
The Nantucket Room Unit - #2
Exterior

The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat
Cape Cod
7.4 out of 10, Good, (6 reviews)
"Cozy clean property that allows pets. Outdoor fire pit area was great and perfectly private. I also loved that the property had a private beach area with lounge chairs. I used the grill and had brunch on the patio table. So nice to enjoy the water from so many parts of the property. Area is quiet and a 7 min walk to Onset Center where you can grab icecream or on some weekdays there’s an even in town. Close to plazas for other needs."
United States
l E.
The price is HK$392
HK$4,082 total
includes taxes & fees
26 Apr - 27 Apr
The Crab Cottage@The Compound Beach Resort Habitat
Property grounds

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dennis
9.0 out of 10, Wonderful, (4 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Outdoor dining

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is HK$1,111
HK$4,760 total
includes taxes & fees
29 Apr - 30 Apr
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Interior

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is HK$1,088
HK$2,069 total
includes taxes & fees
23 Apr - 24 Apr
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Property grounds

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Harwich
10.0 out of 10, Exceptional, (110 reviews)
"The hosts were so accommodating and lovely. The property is adorable and well appointed! Would stay again 100 percent. "
United States
rachel n.
The price is HK$1,174
HK$3,072 total
includes taxes & fees
23 Apr - 24 Apr
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Interior

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

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is HK$1,119
HK$2,842 total
includes taxes & fees
8 May - 9 May
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
Property grounds

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is HK$2,348
HK$4,863 total
includes taxes & fees
23 Apr - 24 Apr
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Sun-loungers

Quaint & Clean Cape Cod Loft

Quaint & Clean Cape Cod Loft
Bourne
10.0 out of 10, Exceptional, (18 reviews)
"Great location! Cute, quiet, neighborhood and so close to the beach. Perfect for our girls mini get away. "
United States
Jessica T.
The price is HK$1,252
HK$2,418 total
includes taxes & fees
19 Apr - 20 Apr
Quaint & Clean Cape Cod Loft
Terrace/patio

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (130 reviews)
"Beautiful room and view, hosts were communicative and check in/out were easy. Would definitely stay here again!"
United States
Alexander L.
The price is HK$1,956
HK$2,998 total
includes taxes & fees
30 Apr - 1 May
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Beach

Cape Cod Oceanside Condo across from beach! Combine World Cup + Beach Holiday!

Cape Cod Oceanside Condo across from beach! Combine World Cup + Beach Holiday!
Dennis
8.6 out of 10, Excellent, (13 reviews)
"Room was as advertised, very close to the beach."
United States
Glen C.
The price is HK$783
HK$1,075 total
includes taxes & fees
3 May - 4 May
Cape Cod Oceanside Condo across from beach! Combine World Cup + Beach Holiday!
Sun-loungers, beach towels

Pond View~ Abuts conservation and walking trails. There is fishing at the pond

Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Dennis
10.0 out of 10, Exceptional, (129 reviews)
"Lovely comfortable place, as described, quiet location and perfectly located for accessing different parts of the Cape."
United States
david s.
The price is HK$1,549
HK$2,006 total
includes taxes & fees
13 May - 14 May
Pond View~ Abuts conservation and walking trails. There is fishing at the pond
Property grounds

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.0 out of 10, Very good, (3 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 HK$1,096
HK$3,108 total
includes taxes & fees
19 Apr - 20 Apr
Charming 3 bed room with magnificent views & large deck
Smart TV, fireplace, books

Classic Cape House Walking Distance to the Beach - Many recent upgrades

Classic Cape House Walking Distance to the Beach - Many recent upgrades
Chatham
9.8 out of 10, Exceptional, (20 reviews)
"Mary was a wonderful host. The house was clean, close to beach and communication was wonderful! A great, relaxing stay!!"
United States
Kathleen T.
The price is HK$2,348
HK$5,929 total
includes taxes & fees
23 Apr - 24 Apr
Classic Cape House Walking Distance to the Beach - Many recent upgrades
Beach nearby

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (44 reviews)
"Great place!"
United States
Michael P.
The price is HK$1,754
HK$3,064 total
includes taxes & fees
20 Apr - 21 Apr
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Beach nearby

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.6 out of 10, Excellent, (8 reviews)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is HK$1,167
HK$4,050 total
includes taxes & fees
26 Apr - 27 Apr
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
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.
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Top Osterville Hotel Reviews

Iris Hotel Cape Cod

Iris Hotel Cape Cod

8/10 Good
"Since the new ownership there have been many updates the past 4 stays. The effort put into the property and amenities is much appreciated. The room is always quiet and clean."
Jeanine 1-night trip
Posted 4 hours ago
Iris Hotel Cape Cod

Find out more about Osterville

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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?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This holiday home rental outside of Osterville is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Osterville?

With 68 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.