Vacation Rentals in Stand Up & Paddle Cape Cod, MA: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  Osterville
  6.  Stand Up & Paddle Cape Cod

Refine your search

Price per night

Amenity Filter

Rating

799 Best Vacation Rentals in Stand Up & Paddle Cape Cod (Starting from $180)

Walk to Shops and Dining Cozy Osterville Cottage
Walk to Shops and Dining Cozy Osterville Cottage
House
Osterville, MA, USA
0.5k from Stand Up & Paddle Cape Cod center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms5 Guests
8.0

Good

1 reviews

$271
Average price / night
Check Availability
New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10
New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10
House
Osterville, MA, 02655, United States
0.4k from Stand Up & Paddle Cape Cod center

AC, Internet, Kitchen, Laundry, No Smoking, Outdoor Grill, Outdoor Space, Patio, TV

4 Bedrooms9 Guests
10.0

Exceptional

4 reviews

$1323
Average price / night
Check Availability
Walk to Main St Osterville Village Gem with Patio
Walk to Main St Osterville Village Gem with Patio
House
Osterville, MA, USA
0.5k from Stand Up & Paddle Cape Cod center

Security/Safety, Internet, Parking, Guest Services, Accessibility, Fireplace/Heating, Child Friendly

1 Bedroom4 Guests
New to Booking
$319
Average price / night
Check Availability
Little Gem walking distance to Osterville Village
Little Gem walking distance to Osterville Village
House
Osterville, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

Internet, Kitchen, Living Area, No Smoking, Outdoor Grill, Patio

2 Bedrooms4 Guests
New to Booking
$393
Average price / night
Check Availability
Cape Breeze Cottage
Cape Breeze Cottage
House
Osterville, MA, USA
0.7k from Stand Up & Paddle Cape Cod center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$304
Average price / night
Check Availability
Walk to Shops & Dining: Cozy Osterville Cottage
Walk to Shops & Dining: Cozy Osterville Cottage
Cottage
Osterville, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Fireplace, Free Parking, Kitchen, Microwave, No Smoking, Patio, TV

2 Bedrooms5 Guests
8.6

Fabulous

11 reviews

$380
Average price / night
Check Availability
55 Wianno Circle Osterville - O Captain My Captain
55 Wianno Circle Osterville - O Captain My Captain
House
Osterville, MA, USA
0.9k from Stand Up & Paddle Cape Cod center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom6 Guests
New to Booking
$638
Average price / night
Check Availability
Osterville Gem Steps to Main St! Relax fireside
Osterville Gem Steps to Main St! Relax fireside
House
Osterville, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$380
Average price / night
Check Availability
Swing Set Plunge pool and large yard await
Swing Set Plunge pool and large yard await
House
Barnstable, MA, USA
1.0k from Stand Up & Paddle Cape Cod center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms8 Guests
8.0

Good

1 reviews

$420
Average price / night
Check Availability
Perfect Family Retreat in Idyllic Osterville. Steps to the town center and beach
Perfect Family Retreat in Idyllic Osterville. Steps to the town center and beach
House
Barnstable, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
New to Booking
$726
Average price / night
Check Availability
Osterville Odyssey
Osterville Odyssey
House
Osterville, MA, USA
2.1k from Stand Up & Paddle Cape Cod center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$337
Average price / night
Check Availability
Charming Cottage Getaway
Charming Cottage Getaway
Cottage
Osterville, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms3 Guests
10.0

Exceptional

61 reviews

$329
Average price / night
Check Availability
161 Bay Lane Centerville Cape Cod - Bay Breeze
161 Bay Lane Centerville Cape Cod - Bay Breeze
House
Centerville, MA, USA
2.3k from Stand Up & Paddle Cape Cod center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Hot tubs, Places to stay

1 Bedroom8 Guests
New to Booking
$2304
Average price / night
Check Availability
Charming cottage near Osterville Village and Dowses beach RPMS094
Charming cottage near Osterville Village and Dowses beach RPMS094
Cottage
Osterville, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms3 Guests
10.0

Exceptional

1 reviews

$493
Average price / night
Check Availability
Bumps River Bungalow
Bumps River Bungalow
House
Centerville, MA, USA
2.4k from Stand Up & Paddle Cape Cod center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis, Places to stay, Family

5 Bedrooms10 Guests
New to Booking
$1064
Average price / night
Check Availability
Osterville - close to town & beach, AC, beach pass
Osterville - close to town & beach, AC, beach pass
House
Barnstable, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$853
Average price / night
Check Availability
Unique A Frame Short Drive to Beach
Unique A Frame Short Drive to Beach
House
Barnstable, MA, USA
2.5k from Stand Up & Paddle Cape Cod center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms10 Guests
New to Booking
$432
Average price / night
Check Availability
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
House
Barnstable, MA, 02655, United States
0.5k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$513
Average price / night
Check Availability
Private Saltwater Pool Game Room near Beaches
Private Saltwater Pool Game Room near Beaches
House
Barnstable, MA, USA
2.5k from Stand Up & Paddle Cape Cod center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

4 Bedrooms8 Guests
New to Booking
$570
Average price / night
Check Availability
Large home in the heart of Osterville Village, sleeps 11
Large home in the heart of Osterville Village, sleeps 11
House
Osterville, MA, 02655, United States
0.6k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms11 Guests
New to Booking
$1125
Average price / night
Check Availability
Shake on the Cape
Shake on the Cape
House
Osterville, MA, USA
2.5k from Stand Up & Paddle Cape Cod center

Wheelchair Accessible, Kitchen, Parking, Air Conditioner, Laundry, Pool, Balcony/Terrace

4 Bedrooms10 Guests
9.0

Fabulous

1 reviews

$824
Average price / night
Check Availability
Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.
Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.
House
Osterville, MA, 02655, United States
0.6k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$792
Average price / night
Check Availability
Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
Osterville Village - New Pool Large Yard + Outdoor Entertaining Area
House
Osterville, MA, 02655, United States
0.6k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Fireplace, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$753
Average price / night
Check Availability
2 Mi to Dowses Beach! Couples Haven in Osterville
2 Mi to Dowses Beach! Couples Haven in Osterville
House
Osterville, MA, 02655, United States
0.7k from Stand Up & Paddle Cape Cod center

AC, Kitchen, Microwave, No Smoking, Outdoor Space, Patio, Toys, TV

1 Bedroom2 Guests
New to Booking
$180
Average price / night
Check Availability
Osterville~Newly Renovated with central AC and beach pass
Osterville~Newly Renovated with central AC and beach pass
House
Osterville, MA, 02655, United States
0.7k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

22 reviews

$391
Average price / night
Check Availability
Dowses Beach pass included • Private 3BR Osterville home near village
Dowses Beach pass included • Private 3BR Osterville home near village
House
Osterville, MA, 02655, United States
0.8k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$602
Average price / night
Check Availability
Impressive Osterville Residence - Ideal Location
Impressive Osterville Residence - Ideal Location
House
Osterville, MA, 02655, United States
0.8k from Stand Up & Paddle Cape Cod center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

6 Bedrooms15 Guests
10.0

Exceptional

1 reviews

$1546
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Stand Up & Paddle Cape Cod.

Where to stay in Stand Up & Paddle Cape Cod? Best neighborhoods & areas

Stand Up & Paddle Cape Cod Vacation Rentals on the Map

Frequently Asked Questions

You can explore 799 verified vacation rentals in Stand Up & Paddle Cape Cod. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Stand Up & Paddle Cape Cod vary depending on the season, property size, and location. Rates typically start from around $180 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Stand Up & Paddle Cape Cod include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Stand Up & Paddle Cape Cod welcome pets. Currently, 32 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Stand Up & Paddle Cape Cod often include amenities such as Balcony/Terrace, Fireplace/Heating, and Kitchen. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.