
Family-friendly holiday rentals in Holden
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Top-rated family-friendly rentals in Holden
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Gather, Cook & Unwind, 3BR, Fireplace
A private resort — without leaving Worcester. Heated pool, fire table, garden courtyard … your own enclosed escape. ★ "Tania’s place was much more than a place….it was a full on fabulous experience." 🏊Heated Pool (to 81F) 🌿 Courtyard w. lounge + garden 🔥Patio w/ Zen fire table* 🍽️ Natural gas + charcoal grills 💧 Reverse osmosis water filter 66” smart TV projector ❄️ Central air conditioning 🔥Indoor gas fireplace 📶300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.
Indoor spacesFamilySleep quality
4.97 out of 5 average rating, 132 reviews
The Tree House at Underhill Hollow
The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.
KitchenIndoor spacesCheck-in
4.96 out of 5 average rating, 451 reviews
Farm Living
We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, donkeys, peacocks, emu, rabbits, dogs, chickens, ducks and wildlife strolling now and then. There’s opportunity to interact with the animals. Pack n play available for little ones upon request and another twin fold up bed. We truly want all of our guest to enjoy all the farm has to offer and enjoy the peacefulness. Please inquire about kayak rentals. We also have a game room available to rent. See photos
FamilyIndoor spacesPool
4.95 out of 5 average rating, 425 reviews
Carriage house apartment
We have a one bedroom apartment at our historic home, Liberty Farm, which is the 2nd oldest house in Worcester Massachusetts and known as the Abby Kelley Foster house to the locals. Recent furniture upgrade in living room, see pictures. Kitchen has all of the amenities: stove, microwave, fridge, disposal and stack-able washer/dryer. Guests may enjoy the grounds in the quiet Tatnuck Square neighborhood, minutes from the Worcester Airport, restaurants, and hiking. House tours upon request.
FamilyKitchenLong stay
4.82 out of 5 average rating, 335 reviews
Spacious 3 Bedroom Home for Family Farm Stay
We welcome you to our farm to enjoy our scenery while making memories at our unique rental home great for groups. Our house rental is part of our property where we invite guests to escape to the farm. This family home is excellent for those looking to relax while away from the ski slopes or simply wanting a space to get away. In the middle of an area with plenty of outdoor activities nearby, we're only 8 miles from Wachusett Mountain Ski Resort and have restaurants within just minutes.
Indoor spacesFamilySleep quality
4.9 out of 5 average rating, 126 reviews
In-law Apartment, Full Kitchen, Near Mt Wachusetts
Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.
FamilyIndoor spacesCheckout
4.98 out of 5 average rating, 228 reviews
Charming Large Entire Home Spacious 3 Bed 2.5 Bath
Make some memories at this unique and family-friendly place. A charming home with an eclectic style has tall ceilings, wide open spaces and just that home-sweet-home, comfy feel. Enjoy your morning coffee on the front farmers porch. A jacuzzi bath in the master bathroom. Open the windows and listen to the bird singing in the city. The sunsets are a must and can be seen from the dining room table every night. It’s unreal, really. Centrally located and only 2 minutes away from highways.
Indoor spacesKitchenValue
5.0 out of 5 average rating, 117 reviews
Centrally Located Apartment in Worcester
This first-floor unit in a charming 1910 duplex offers modern comfort and unbeatable convenience. Located within half a mile of Worcester State University and a grocery store, and within walking distance of restaurants and shops, it’s perfect for any lifestyle. The updated space features lightning-fast 1 Gbps WiFi, two workspaces, off-street parking for one car, and plenty of on-street parking. Ideal for both work and relaxation, this home is fully equipped for a comfortable stay.
FamilyKitchenHospitality
4.96 out of 5 average rating, 114 reviews
Farm stay in a Historic Ski Lodge turned Barn
Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the horses and ponies and see the chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.
KitchenIndoor spacesBeach
4.9 out of 5 average rating, 544 reviews
Quiet country retreat with modern conveniences
Our mountain-view farmhouse sits on a 5 acre knoll, 300' from a quiet country road, surrounded by the sights and sounds of quintessential New England. The location of the property strikes a perfect balance between seclusion and convenience with access to hiking, kayaking, biking, parks, restaurants, grocery, and shopping close by. Restaurant food delivery of local favorites for Japanese (including sushi), Chinese, pizza, sub, salads, etc is available.
Indoor spacesKitchenGetting around
4.93 out of 5 average rating, 242 reviews
Modern 2 Bedroom Basement Suite
Modern, Comfortable, Spacious 1st Floor Basement apartment; open layout concept. Located 5 minutes from Worcester State University and 15 minutes to all other Universities/Colleges (WPI, Assumption, Anna Maria, Mass College of Pharmacy, UMASS Medical and more.) 10 minutes from I-290 & 15 minutes to the Mass Pike- I-90, RT 20, RT 146, I-495, & I 395. Great alternative to local hotels, local college graduation season, or even a vacation getaway.
KitchenIndoor spacesSleep quality
4.88 out of 5 average rating, 160 reviews
Spacious 1 Bedroom near Colleges, DCU+Parking
Bright and spacious second floor one bedroom apartment in Highland St / WPI area, located near WPI, Becker College, Elm Park, Highland Street, stores and restaurants, MCPHS, DCU. Huge bedroom with walk-in closet, renovated bathroom and eat-in kitchen laundry in the unit, spacious hallway, charming shared balcony, one off street parking space included. The whole group will enjoy easy access to everything from this centrally located place.
Indoor spacesFamilyLayout
4.96 out of 5 average rating, 108 reviewsPopular amenities for Holden family-friendly rentals
Family-friendly home rentals with a hot tub

1790 Stone Manor Farm
KitchenFamilyOutdoor spaces
4.96 out of 5 average rating, 166 reviews
Rustic Farmette Studio w/yearround Hot Tub
FamilyIndoor spacesGrill
5.0 out of 5 average rating, 264 reviews
Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views
FamilyIndoor spacesCondition
4.96 out of 5 average rating, 156 reviews
Hopkinton Mass 3+ Bedrooms - Great location!
Indoor spacesKitchenAccess
4.95 out of 5 average rating, 180 reviews
Private sanctuary in the city w/ patio & backyard
FamilyIndoor spacesTV
4.95 out of 5 average rating, 140 reviews
Luxury By The Lake
FamilyKitchenBeach
4.85 out of 5 average rating, 195 reviews
Lakefront Beauty with Hot Tub
FamilyIndoor spacesGrill
4.96 out of 5 average rating, 109 reviews
Lakefront Cottage Complete with Kayaks!
Indoor spacesFamilyCleanliness
4.89 out of 5 average rating, 116 reviewsFamily- and pet-friendly home rentals

COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
FamilyIndoor spacesAir conditioning
4.86 out of 5 average rating, 176 reviews
Million-Dollar View - Great Location/Sleeps 9
KitchenFamilyGetting around
4.9 out of 5 average rating, 136 reviews
Lakefront, view of ski mtn, fireplace, sauna
Indoor spacesFamilySkiing
4.89 out of 5 average rating, 240 reviews
Luxury Spacious 2BR • King & Queen Beds • 2 Baths
FamilyKitchenBathroom
4.81 out of 5 average rating, 120 reviews
Unique and Private Cottage in Worcester
Indoor spacesKitchenBiking
4.9 out of 5 average rating, 140 reviews
Trainmaster's Inn - Caboose
FamilyIndoor spacesOutdoor spaces
4.94 out of 5 average rating, 142 reviews
Little House Inn - Brimmy - Private Home
Indoor spacesFamilyGetting around
4.87 out of 5 average rating, 323 reviews
Clean & Cozy 2BR | Great Central Location
KitchenFamilyBathroom
4.9 out of 5 average rating, 150 reviewsFamily-friendly home rentals with a pool

Farmhouse Guest Apartment
FamilyKitchenHiking
5.0 out of 5 average rating, 110 reviews
Cedar Ridge: House
Indoor spacesKitchenLong stay
4.92 out of 5 average rating, 278 reviews
Triggers Cabin
Indoor spacesFamilyQuiet
4.93 out of 5 average rating, 192 reviews
Great country getaway
FamilyIndoor spacesGrill
4.87 out of 5 average rating, 187 reviews
Exquisite 1 Bedroom Suite-Charming,W/Private Entry
Indoor spacesKitchenGetting around
4.78 out of 5 average rating, 104 reviews
Pool•1000mbpsWiFi•DeepTub•Fireplace•Full Kitchen
Indoor spacesFamilyCondition
4.86 out of 5 average rating, 28 reviews
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
FamilyIndoor spacesCondition
4.84 out of 5 average rating, 56 reviews
Metrowest Family Retreat
KitchenFamilyCheck-in
4.81 out of 5 average rating, 21 reviewsDestinations to explore
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- Fenway Park
- Harvard University
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Six Flags New England
- Freedom Trail
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- MIT Museum
- Harvard Square
- Tufts University
- Monadnock State Park
- Quincy Market
- Snhu Arena
- Massachusetts Institute of Technology
- Roger Williams Park Zoo
- Prudential Center





