56min by car
Wachusett Mountain Ski Area
27 trails and 8 lifts below a 2,006-foot summit, with rentals, lessons and night-skiing tickets.
It's a day trip by car. Check the snow report and ticket page before you leave.
The house has heat, a full kitchen and a table for eight. In winter a ski mountain is under an hour away, an open-hearth feast is 7 minutes down Route 9, and the porch windows face west across the lake.
Dates, hours and prices come from each organizer's website and were checked on November 11, 2026. Winter plans change with the weather, so follow the links before you drive.

The house has heat, Wi-Fi, a full kitchen with a gas range and a dishwasher, and a dining table that seats eight. The living room has two sofas and a wall-mounted TV, and the glassed-in porch and the breakfast bar look out toward the lake.
Upstairs, the shared bath has a freestanding soaking tub and a separate shower. Board games and extra blankets are on the shelves in the queen room. Use the patio fire pit only when the hosts' instructions and current local fire restrictions permit. An adult must tend and fully extinguish any permitted fire.



Minutes by car without traffic. Plain numbers are routed from the house. Numbers marked ~ are rounded from West Brookfield center.
56min by car
27 trails and 8 lifts below a 2,006-foot summit, with rentals, lessons and night-skiing tickets.
It's a day trip by car. Check the snow report and ticket page before you leave.
~55min by car
A small hill for first turns, and home of the TubaSlide snow-tubing park with up to 12 lanes, 2 lifts and more than 200 tubes.
Tubers must be at least 6 years old and 42 inches tall. Weekend and holiday sessions run two hours, starting at 10 AM, noon and 2 PM, and they can sell out.
9min by car
Three miles of trails and woods roads around the rock shelter and Carter Pond. Free, open sunrise to sunset, dogs on a leash.
The lot is plowed, though it can take one to three days after a storm. During Route 9 construction the Trustees send visitors to the Pierce Road lot, so check their page first.
~15min by car
About three flat miles of old railbed near the Ware River, cared for by the East Quabbin Land Trust, which welcomes cross-country skiers.
Park at the former New Braintree station site on Hardwick Road, and bring your own skis or snowshoes.
29min by car
A 1,400-acre state park with 12 miles of trails. The state lists cross-country skiing among its activities.
Snowmobiles use the park too, so stay alert on the wider trails.
~30min by car
An Army Corps of Engineers park with more than three miles of trails open all year. The Corps lists cross-country skiing, snowshoeing, sledding and ice skating among its winter uses.
The entry gates close for the winter, so expect to walk in from the road.
31min by car
Reservoir overlooks at Winsor Dam and Enfield Lookout, where winter is the classic season for spotting bald eagles. Cross-country skiing is allowed on designated routes only.
No dogs, even in a parked car. Vehicle gates were closing at 5 PM when we checked, and the park is closed on Thanksgiving, Christmas and New Year's Day.
~45min by car
A 12,000-square-foot outdoor rink behind City Hall, with skate rentals for $6.
Its page says the rink reopens in December 2026. It closes in bad weather, so check before you go.
~40min by car
FMC Ice Sports runs public skating at Horgan Arena in Auburn and Buffone Arena in Worcester. Admission is $10 and skate rentals are $10.
Session times change by day. Pick the rink on FMC's schedule page.
MassWildlife describes the 320-acre pond as a good panfish water that anglers also fish through the ice, with abundant white perch plus yellow perch, black crappie, chain pickerel and bass. Anglers 15 and older need a Massachusetts freshwater fishing license.
Nobody checks the ice at the house or on the lake, and we can't tell you it is safe. The state's guidance is to treat all ice as potentially dangerous, measure it yourself, look for at least four inches of clear, solid ice before walking on it, never go out alone and keep children within reach. The town adds that conditions change from day to day and that anyone on its lakes is there at their own risk.
Message us on Airbnb before you plan anything on the lake in winter, and read the guidance first: MassWildlife on ice fishing and ice safety, the state's page for the pond and the town's notice on using its lakes.
7min by car
A 1700s-style meal cooked at a fieldstone hearth. Prime rib turns on a roasting jack, chowder simmers in an iron cauldron, and the afternoon includes mulled wine or cider, apple pie and a horse-drawn wagon or sleigh ride when the weather allows. $89 per person, tax and gratuity included.
Feasts run on Friday and Saturday evenings and Sunday afternoons from November to April, by advance ticket only. Check the inn’s ticket calendar before choosing your stay; feast tickets and lodging are booked separately.
26min by car
The 1830s village lit and decorated for the holidays, on select days from November 27 to December 27, 2026: Friday to Sunday through December 20, then December 23, 26 and 27, from 2 to 8 PM. Two Candlelight Thursdays, December 10 and 17, run from 4 to 8 PM with a limited number of $12 tickets.
It needs its own ticket, and early-bird prices end November 26. The Village is closed on December 24 and 25, and to daytime visits from November 15 to the end of the year.
5min by car
The town's 34th annual holiday fair, on Sunday, December 6, 2026, from 10 AM to 7 PM.
The town posts a parking and shuttle-bus plan. Check its page for the day's schedule.
~60min by car
This year's display, Fantastical Forest, runs from November 21, 2026 to January 3, 2027, 4 to 10 PM. Adult tickets are $26, or $29 on peak nights.
Reserve tickets ahead and check the calendar for closed nights. By day the garden's conservatories are open 10 AM to 5 PM.
~50min by car
A drive-through light display, from November 25, 2026 to January 3, 2027, starting at 5 PM. Admission is per car: $30 through December 27, then $20, plus a $2 ticket fee.
Closed November 30 and December 1. Tickets must be bought in advance.
~45min by car
The theatre's 19th annual production runs from December 17 to 23, 2026, with no show on December 21, in its 2,300-seat historic house downtown. Before the December 18, 19 and 20 shows, a free winter festival fills the plaza outside, no ticket needed. The Nutcracker plays November 27 to 29.
Buy tickets from the theatre's own page.
Late winter brings sugaring season, from about late February into early April. Old Sturbridge Village has run a working sugar camp on March weekends in past years. Its 2027 dates weren't posted when we checked, so look at its calendar in February.
~45min by car
Open Wednesday to Sunday, 10 AM to 4 PM. Adults pay $22, and visitors 17 and under are free. Its winter show, "Beasts of Legend: Animals in East Asian Art," runs from November 21, 2026 to February 21, 2027.
A campus construction project means some galleries may be closed. The museum lists current closures on its site.
45min by car
A science and nature museum with hands-on indoor exhibits and a planetarium, plus outdoor trails and wildlife habitats.
Part of the visit is outdoors, so dress for it.
~50min by car
Five museums on one campus under one admission, including The Amazing World of Dr. Seuss and the science museum with its planetarium. Open Tuesday to Saturday 10 to 5 and Sunday 11 to 5. The 17th annual gingerbread exhibition, on a superheroes theme this year, runs from November 27, 2026 to January 3, 2027.
Closed Mondays.
~50min by car
Basketball's museum, at 1000 Hall of Fame Avenue in the city where the game was invented.
Hours change by season, so check before you go.
~45min by car
Minor-league hockey downtown, with 36 home games in the season that began in October 2026.
Check the schedule for home dates.
29min by car
A brewery and taproom at 129 Sturbridge Road. Posted hours start at 11 AM daily and run to 9 PM Monday to Thursday, 10 PM Friday and Saturday and 8 PM Sunday.
Bring photo ID. Closed on Thanksgiving and Christmas Day.
15min by car
A family orchard since 1918 whose store stays open all year, 9 AM to 5 PM, with apples, bakery items, fudge and holiday pies to order.
Pick-your-own returns with apple season.
For dinner out, Salem Cross Inn's restaurant and tavern open Thursday to Saturday from 4 to 8 PM and Sunday from noon to 5, 7 minutes from the house. The Publick House tap room in Sturbridge, 26 minutes away, is built around an open hearth. More on Salem Cross Inn
Check in after 3 PM with your keypad code. Stock up at Price Chopper in Spencer, 22 minutes from the house and open until 11 PM, or have dinner at Salem Cross Inn, open 4 to 8 PM on Fridays.
Ski Wachusett or ride the tubes at Ski Ward, both under an hour away. From late November to late December, Christmas by Candlelight at Old Sturbridge Village runs from 2 to 8 PM. Back at the house there are board games, the soaking tub and s'mores at the fire pit.
Checkout is by noon. If you hold Fireplace Feast tickets, Sunday feasts start at 12:30 PM, 7 minutes away. Otherwise walk Rock House Reservation and stop at the Brookfield Orchards country store.
The house is booked through Airbnb from this website, where you'll find the calendar, the price for your dates and guest reviews.