Family-Friendly Vacation Rentals in Cape Cod Rail Trail, MA: Compare 10+ Sites & Save

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  2. Family Vacation Rentals
  3.  USA

  4.  Massachusetts

  5.  South Dennis
  6.  Cape Cod Rail Trail

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808 Best Family Vacation Rentals in Cape Cod Rail Trail (Starting from $190)

Gorgeous Home 1 mile to Beach and near Cape Cod Bikepath
Gorgeous Home 1 mile to Beach and near Cape Cod Bikepath
House
Dennis, MA, USA
0.5k from Cape Cod Rail Trail center

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

3 Bedrooms8 Guests
New to Booking
$676
Average price / night
Check Availability
Luxury Award Winning Sea Captain’s House
Luxury Award Winning Sea Captain’s House
House
Dennis, MA, 02660, United States
0.5k from Cape Cod Rail Trail center

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

6 Bedrooms12 Guests
New to Booking
$1344
Average price / night
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Thayer Thicket
Thayer Thicket
House
South Dennis, MA, USA
0.7k from Cape Cod Rail Trail center

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

3 Bedrooms7 Guests
7.3

Good

3 reviews

$513
Average price / night
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Near Mayflower Beach! 4 Bedroom 2.5 Bath Home with Central A/C
Near Mayflower Beach! 4 Bedroom 2.5 Bath Home with Central A/C
House
South Dennis, MA, 02660, United States
0.6k from Cape Cod Rail Trail center

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

4 Bedrooms11 Guests
9.8

Exceptional

10 reviews

$1854
Average price / night
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Waterfront Incredible Views and Private Dock
Waterfront Incredible Views and Private Dock
House
Yarmouth, MA, USA
1.3k from Cape Cod Rail Trail center

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

6 Bedrooms14 Guests
New to Booking
$1075
Average price / night
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Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay
Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay
House
South Dennis, MA, 02660, United States
1.3k from Cape Cod Rail Trail center

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

2 Bedrooms6 Guests
9.6

Exceptional

71 reviews

$350
Average price / night
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Family Dennis retreat with sauna firepit private pool
Family Dennis retreat with sauna firepit private pool
House
Dennis, MA, USA
1.3k from Cape Cod Rail Trail center

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

1 Bedroom10 Guests
New to Booking
$3190
Average price / night
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NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
House
Dennis, MA, 02660, United States
1.4k from Cape Cod Rail Trail center

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

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$338
Average price / night
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3 Mi to Beach Historic Farmhouse on Cape Cod!
3 Mi to Beach Historic Farmhouse on Cape Cod!
House
South Dennis, MA, USA
1.3k from Cape Cod Rail Trail center

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

4 Bedrooms8 Guests
8.5

Very Good

2 reviews

$305
Average price / night
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Big House in Heart of Cape.  Close to Everything!
Big House in Heart of Cape. Close to Everything!
House
South Dennis, MA, 02660, United States
1.6k from Cape Cod Rail Trail center

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

4 Bedrooms8 Guests
10.0

Exceptional

123 reviews

$457
Average price / night
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Walk to Beach Dennis Cottage with Deck!
Walk to Beach Dennis Cottage with Deck!
House
South Dennis, MA, USA
1.4k from Cape Cod Rail Trail center

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

3 Bedrooms8 Guests
New to Booking
$666
Average price / night
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Swan Pond Cottage, Waterfront Central A/C,  Open Floor Plan
Swan Pond Cottage, Waterfront Central A/C, Open Floor Plan
Cottage
South Dennis, MA, 02660, United States
1.7k from Cape Cod Rail Trail center

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

2 Bedrooms4 Guests
9.8

Exceptional

231 reviews

$348
Average price / night
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The White Pillars
The White Pillars
House
South Dennis, MA, USA
1.4k from Cape Cod Rail Trail center

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

7 Bedrooms12 Guests
New to Booking
$1024
Average price / night
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Modern, coastal cottage, AC, beaches, tennis, golf, restaurants, bike trail
Modern, coastal cottage, AC, beaches, tennis, golf, restaurants, bike trail
House
Dennis, MA, 02660, United States
1.7k from Cape Cod Rail Trail center

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

3 Bedrooms5 Guests
10.0

Exceptional

3 reviews

$330
Average price / night
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Dennis Port Delight
Dennis Port Delight
House
Dennis Port, MA, USA
1.4k from Cape Cod Rail Trail center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$565
Average price / night
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Amazing Lakefront Property, Private Dock, Direct Access to Water, New Hot Tub/AC
Amazing Lakefront Property, Private Dock, Direct Access to Water, New Hot Tub/AC
Cottage
Dennis Port, MA, 02639, United States
1.9k from Cape Cod Rail Trail center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

96 reviews

$814
Average price / night
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Freydis Glen
Freydis Glen
House
South Dennis, MA, USA
1.5k from Cape Cod Rail Trail center

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

3 Bedrooms6 Guests
8.0

Good

1 reviews

$414
Average price / night
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Charming, newly renovated house, a few steps from bike path.
Charming, newly renovated house, a few steps from bike path.
House
Dennis Port, MA, 02639, United States
2.0k from Cape Cod Rail Trail center

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

3 Bedrooms6 Guests
9.0

Fabulous

24 reviews

$558
Average price / night
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Newly Updated Home Stone Patio & Fire Pit
Newly Updated Home Stone Patio & Fire Pit
House
Dennis, MA, USA
1.6k from Cape Cod Rail Trail center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms7 Guests
9.5

Superb

2 reviews

$610
Average price / night
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Dennisport 4 Bed w/access to Swan Pond /across the street. Great for Kayaking!
Dennisport 4 Bed w/access to Swan Pond /across the street. Great for Kayaking!
House
Dennis Port, MA, 02639, United States
2.1k from Cape Cod Rail Trail center

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

4 Bedrooms8 Guests
10.0

Exceptional

31 reviews

$437
Average price / night
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Beachfront - Sauna - Screened Patio - 2 King Beds - Dogs Encouraged!
Beachfront - Sauna - Screened Patio - 2 King Beds - Dogs Encouraged!
House
Dennis, MA, 02660, United States
2.2k from Cape Cod Rail Trail center

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

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$1073
Average price / night
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Best of Both Worlds on Swan Pond in Dennisport
Best of Both Worlds on Swan Pond in Dennisport
Cottage
Dennis Port, MA, 02639, United States
2.2k from Cape Cod Rail Trail center

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

4 Bedrooms8 Guests
9.8

Exceptional

71 reviews

$456
Average price / night
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 Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
Cottage
South Yarmouth, MA, 02664, United States
2.2k from Cape Cod Rail Trail center

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

1 Bedroom4 Guests
9.4

Superb

30 reviews

$190
Average price / night
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NEW Luxury Cape House -10min to Beaches + Golf!!
NEW Luxury Cape House -10min to Beaches + Golf!!
House
Dennis, MA, 02660, United States
2.4k from Cape Cod Rail Trail center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
9.6

Exceptional

7 reviews

$569
Average price / night
Check Availability
#Game Room, Wi-Fi, Bikes, Beach  Supplies, Quiet Street, Central AC\\Heat
#Game Room, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\\Heat
House
Harwich, MA, 02645, United States
2.4k from Cape Cod Rail Trail center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

4 Bedrooms9 Guests
10.0

Exceptional

130 reviews

$493
Average price / night
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The Swan River House
The Swan River House
House
dennis, MA, 02660, United States
2.4k from Cape Cod Rail Trail center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

4 Bedrooms10 Guests
9.6

Exceptional

23 reviews

$830
Average price / night
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Beautiful Waterfront-Relaxin' on the River!
Beautiful Waterfront-Relaxin' on the River!
House
South Dennis, MA, 02660, United States
2.4k from Cape Cod Rail Trail center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms7 Guests
10.0

Exceptional

64 reviews

$437
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 Family Vacation Rentals in Cape Cod Rail Trail.

Where to stay in Cape Cod Rail Trail? Best neighborhoods & areas

Cape Cod Rail Trail Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 808 verified family-friendly vacation rentals in Cape Cod Rail Trail. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Cape Cod Rail Trail vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $190 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Cape Cod Rail Trail offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Cape Cod Rail Trail are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Cape Cod Rail Trail often include amenities such as Child Friendly, Fireplace/Heating, and View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.