Family-Friendly Vacation Rentals in Mechanicsville, NY: Compare 10+ Sites & Save

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41 Best Family Vacation Rentals in Mechanicsville (Starting from $132)

2 Bed Berkshire Getaway @ Stephentown Hotel
2 Bed Berkshire Getaway @ Stephentown Hotel
Apartment
Stephentown, NY, USA
3.5k from Mechanicsville center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
9.4

Superb

8 reviews

$172
Average price / night
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 A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
House
Stephentown, NY, 12169, United States
1.5k from Mechanicsville center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.6

Exceptional

33 reviews

$258
Average price / night
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5 Bed/3 bath Apt Near Jiminy Peak Berkshires
5 Bed/3 bath Apt Near Jiminy Peak Berkshires
Apartment
Stephentown, NY, USA
3.5k from Mechanicsville center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Self-catering

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$494
Average price / night
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The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
House
Stephentown, NY, 12168, United States
3.5k from Mechanicsville center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, No Smoking

9 Bedrooms28 Guests
10.0

Exceptional

3 reviews

$1070
Average price / night
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Berkshires Studio Apartment at the Stephentown Hotel
Berkshires Studio Apartment at the Stephentown Hotel
Apartment
Hancock, NY, USA
3.5k from Mechanicsville center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Ski resorts

1 Bedroom4 Guests
New to Booking
$142
Average price / night
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2 Bed Berkshire Getaway minutes to Jiminy Peak Ski
2 Bed Berkshire Getaway minutes to Jiminy Peak Ski
Apartment
Hancock, NY, USA
3.5k from Mechanicsville center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family, Ski resorts

2 Bedrooms6 Guests
9.8

Exceptional

8 reviews

$132
Average price / night
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Sleeps 40 • Heated Pool • Hot Tub • Game Room | Brookside Mountain Retreat
Sleeps 40 • Heated Pool • Hot Tub • Game Room | Brookside Mountain Retreat
House
Stephentown, NY, 12168, United States
5.8k from Mechanicsville center

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

13 Bedrooms40 Guests
New to Booking
$2363
Average price / night
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Cabin Perfect for Nature Lovers
Cabin Perfect for Nature Lovers
House
Stephentown, NY, USA
4.0k from Mechanicsville center

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

3 Bedrooms6 Guests
New to Booking
$175
Average price / night
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Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond
House
Stephentown, NY, 12168, United States
6.7k from Mechanicsville center

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

3 Bedrooms8 Guests
10.0

Exceptional

38 reviews

$391
Average price / night
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Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak
Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak
House
Hancock, MA, USA
7.8k from Mechanicsville center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

6 Bedrooms18 Guests
9.8

Exceptional

7 reviews

$487
Average price / night
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Cottage in the Clouds With Mountain Views
Cottage in the Clouds With Mountain Views
Cottage
New Lebanon, NY, 12125, United States
7.3k from Mechanicsville center

Balcony, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms4 Guests
9.4

Superb

3 reviews

$383
Average price / night
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Quiet All-Season Creekside Escape in Upstate!
Quiet All-Season Creekside Escape in Upstate!
House
North Hancock, NY, USA
9.0k from Mechanicsville center

Security/Safety, Internet, Accessibility, Parking, Fireplace/Heating, Sports/Activities, Guest Services

1 Bedroom6 Guests
New to Booking
$297
Average price / night
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Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy Peak
House
Hancock, MA, 01237, United States
7.8k from Mechanicsville center

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

6 Bedrooms17 Guests
10.0

Exceptional

19 reviews

$1148
Average price / night
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Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Apartment
Mechanicsville, Stephentown, New York, USA
9.5k from Mechanicsville center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals

2 Bedrooms8 Guests
9.0

Fabulous

26 reviews

$251
Average price / night
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Enchanting Modern Farmhouse with Picturesque Views
Enchanting Modern Farmhouse with Picturesque Views
House
Sand Lake, NY, 12153, United States
8.6k from Mechanicsville center

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

4 Bedrooms9 Guests
10.0

Exceptional

20 reviews

$466
Average price / night
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Mountain View Suite on Jiminy Peak Ski On Off -New
Mountain View Suite on Jiminy Peak Ski On Off -New
Apartment
Hancock, MA, USA
9.8k from Mechanicsville center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
9.4

Superb

19 reviews

$335
Average price / night
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Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort
House
Hancock, MA, 01237, United States
9.3k from Mechanicsville center

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

3 Bedrooms8 Guests
9.8

Exceptional

19 reviews

$383
Average price / night
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1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor
1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor
Apartment
Hancock, MA, USA
9.8k from Mechanicsville center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Ski resorts

1 Bedroom4 Guests
7.7

Good

6 reviews

$335
Average price / night
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Charming Barn Home Near Jiminy Peak – 4BR on 7+ Private Acres
Charming Barn Home Near Jiminy Peak – 4BR on 7+ Private Acres
House
Hancock, MA, 01237, United States
9.4k from Mechanicsville center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$530
Average price / night
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Cozy Ski in out Cabin in Berkshire Resort
Cozy Ski in out Cabin in Berkshire Resort
House
Hancock, MA, USA
9.8k from Mechanicsville center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cabins, Cottages, Pet-friendly

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$323
Average price / night
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Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗
Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗
Condo
Hancock, MA, 01237, United States
9.5k from Mechanicsville center

AC, Arcade, Balcony, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$210
Average price / night
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Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Condo
Hancock, MA, 01237, United States
9.5k from Mechanicsville center

AC, Arcade, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

2 Bedrooms4 Guests
9.8

Exceptional

21 reviews

$257
Average price / night
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SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Condo
Hancock, MA, 01237, United States
9.7k from Mechanicsville center

AC, Arcade, Balcony, Breakfast Available, Dryer, Elevator, Fireplace, Fitness Equipment, Free Parking

3 Bedrooms10 Guests
10.0

Exceptional

43 reviews

$317
Average price / night
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Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak
Condo
Hancock, MA, 01237, United States
9.7k from Mechanicsville center

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

3 Bedrooms10 Guests
New to Booking
$454
Average price / night
Check Availability
Vacation Village in the Berkshires
Vacation Village in the Berkshires
Condo
276 Brodie Mountain Rd, Williamstown, MA, 01237, United States
9.8k from Mechanicsville center

AC, Arcade, Business Services, Fireplace, Fitness Equipment, Free Parking, Frontdesk 24 Hour, Heater, Internet

1 Bedroom4 Guests
8.8

Fabulous

2324 reviews

$165
Average price / night
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🌞Views! 2m2Ski! 1BR King Condo! OpenLR/DR/K! FP HPool,Jacuzzi, Gym+KidsStuff🌞!
🌞Views! 2m2Ski! 1BR King Condo! OpenLR/DR/K! FP HPool,Jacuzzi, Gym+KidsStuff🌞!
Condo
Hancock, MA, 01237, United States
9.8k from Mechanicsville center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

1 Bedroom4 Guests
4.0

Review score

1 reviews

$202
Average price / night
Check Availability
Ski season is here!
Ski season is here!
Condo
Hancock, MA, 01237, United States
9.8k from Mechanicsville center

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

2 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$539
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 Mechanicsville.

Mechanicsville Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 41 verified family-friendly vacation rentals in Mechanicsville. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Mechanicsville vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $132 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Mechanicsville 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 Mechanicsville 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 Mechanicsville often include amenities such as Child Friendly, Internet, and Fireplace/Heating. 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.