Osterville Holiday Rentals

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Holiday Rentals in Osterville

Newly Renovated Guest House For 10 Near The Beach!

10.0 out of 10, Exceptional, (3)
"Our stay in Harwich was exceptionally comfortable and convenient, ideal for a larger group or family. The multiple spacious bedrooms provided ample private space, complemented by the practical 2.5 baths. We particularly appreciated the expansive backyard, perfect for outdoor activities, and the generous parking—the driveway easily accommodated four cars, with extra space alongside for two more—making arrivals and departures stress-free. This property truly felt like a home away from home,...
The price is AU$1,693
includes taxes & fees
30 June - 1 July
Newly Renovated Guest House For 10 Near The Beach!

Luxe Lakefront Retreat ★ Sauna ★ Media Rm ★ Kayaks ★ Bikes ★ Steps to Bike-Path★

The price is AU$2,146
includes taxes & fees
17 July - 18 July
Luxe Lakefront Retreat ★ Sauna ★ Media Rm ★ Kayaks ★ Bikes ★ Steps to Bike-Path★

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

9.6 out of 10, Exceptional, (40)
"We enjoyed everything about our stay. Charming house, great location. Looking forward to staying there again in the future."
The price is AU$921
includes taxes & fees
30 June - 1 July
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

The price is AU$1,317
includes taxes & fees
9 July - 10 July
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

By the Sea Guests Bed and Breakfast and Suites - Elenis' Suite

The price is AU$1,219
includes taxes & fees
29 June - 30 June
By the Sea Guests Bed and Breakfast and Suites - Elenis' Suite

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

10.0 out of 10, Exceptional, (154)
"Place was adorable perfect for what we needed. Perfect location, centralized for all your needs and wants"
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Walk to Sea Street Beach! Firepit| Dogs OK| A/C!

9.6 out of 10, Exceptional, (4)
"Our vacation at Kim and Dave’s cottage was fabulous, location to the beach and restaurants were exactly what we needed, fenced in back yard with a deck a fire-pit and grill is perfect if you’re bringing young ones or a fur-baby… thank you again to Dave and Kim,"
The price is AU$2,161
includes taxes & fees
26 July - 27 July
Walk to Sea Street Beach! Firepit| Dogs OK| A/C!

Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

10.0 out of 10, Exceptional, (6)
"Perfect, clean, the property had everything we needed. I’d stay again."
Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Lobster Pot Getaway - 5-Min Walk to the Beach

Lobster Pot Getaway - 5-Min Walk to the Beach

Lobster Pot & Glendon Midship Cottages - 5-Min Walk to Beach

Lobster Pot & Glendon Midship Cottages - 5-Min Walk to Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

9.0 out of 10, Wonderful, (41)
"Location was unmatched! Easy beach access and activities all around."
The price is AU$791
includes taxes & fees
6 July - 7 July
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Charming condo efficiency in peaceful Dennisport with WiFi, AC

The price is AU$417
includes taxes & fees
9 July - 10 July
Charming condo efficiency in peaceful Dennisport with WiFi, AC

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

9.8 out of 10, Exceptional, (9)
"We had a great vacation & experience at this rental house! It was clean, had everything we needed and is located in a quiet neighborhood with easy access to the highway."
The price is AU$1,083
includes taxes & fees
7 July - 8 July
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

Cozy Coastal Retreat West Dennis

2.0 star property
The price is AU$1,254
includes taxes & fees
8 July - 9 July
Cozy Coastal Retreat West Dennis

Coastal Haven in West Dennis

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was a great place to stay and relax, just a short walk to the beach and quick drive to great restaurants and activities. Highly recommend!!"
Coastal Haven in West Dennis

New Home in the heart of South Dennis

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great location - easy accesst o RT. 6 and various beaches. Host was very accommodating and easy to communicate with. Would definitely stay again."
New Home in the heart of South Dennis

3 Mi to Beach: Historic Farmhouse on Cape Cod!

The price is AU$1,134
includes taxes & fees
6 July - 7 July
3 Mi to Beach: Historic Farmhouse on Cape Cod!

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

West Dennis Central - 5 bed, 3 bath, 2 kitchen huge yard! Two hot tubs!

9.4 out of 10, Exceptional, (20)
"The house is very cute and had everything we needed. The location is great and the owner was super responsive."
The price is AU$2,379
includes taxes & fees
9 July - 10 July
West Dennis Central - 5 bed, 3 bath, 2 kitchen huge yard! Two hot tubs!
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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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?

Walk To Beach - Comfortable 2BR Cottage: This holiday home rental outside of Osterville is located near the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a private garden.

How many holiday rentals are there in Osterville?

With 77 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.