Holiday rentals in Sturbridge

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Top-rated holiday rentals in Sturbridge

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Guest favourite

Home in Sturbridge

4.96 out of 5 average rating, 173 reviews

Modern Lakeview House -Chef's Kitchen, Strong Wifi

This house has clean, light, modern design, full of unique details you'll love. Like a large modern kitchen, spa bathroom w/ jacuzzi tub, deck w/ lake view. A few steps from Cedar Lake beach, tennis, playgrounds. Walk to downtown Sturbridge restaurants or cook in our stocked chef's kitchen full of gadgets. Perfect for a "stay-cation" or to work from new location. Visit local Craft Breweries (Treehouse Brewing) and natural trails. A getaway 60min to Boston, 40min to Hartford, 20min to Worcester.

5–12 Jan

$285 SGD per night

Guest favourite

Farm stay in Southbridge

4.98 out of 5 average rating, 163 reviews

High Grass Farm

Get cozy in front of the fireplace and enjoy a romantic getaway in our beautiful and historic old house. One of the top 16 farm stays in New England! Our 1780's farmhouse has been completely renovated and retains its rustic country feel. Experience early American period life with only a few modern conveniences (e.g. full laundry and 5G wi-fi). Our secluded setting on 19 acres in southern Mass is minutes from I-90 and I-84, and borders CT, Old Sturbridge Village and the Westville recreation area.

1–8 Nov

$237 SGD per night

Guest favourite

Cottage in Sturbridge

4.96 out of 5 average rating, 122 reviews

Cedar Sunrise

Welcome to Cedar Lake. Come enjoy the lake and all it has to offer while staying in this cottage at the waters edge. This home may be small, but it offers a full kitchen with microwave, gas stove, Keurig and full size refrigerator. Open concept living, dining and kitchen. One bedroom with queen size bed, an open loft with a twin size bunk bed with trundle and a pullout couch in the living room. Full size bathroom with tub, washer & dryer on site. Enjoy grilling on the deck and soaking up the sun

29 Sep – 6 Oct

$327 SGD per night

Guest favourite

Home in Sturbridge

4.95 out of 5 average rating, 154 reviews

Sturbridge MA 3 BR 2 1/2 Bath Home on Cedar Lake

Fully equipped w/open lake view living space w/gas fpl. Direct access to Lake w/private dock, (2) kayaks, decks, patio, grill & fire pit. Pvt master bed/bath and 2nd bed w/lake view/deck access. Base rate up to 5 people. $50/each add pers-night max 8 total. 4th bed is futon in part finished walkout bsmt/concrete floor. Min 3 night stay pref. Base weekday $315, Weekend $365. Premium rates seasonally/holidays. Local tax added by AirBnB. Ck-out 11 AM, Ck-in 3 PM unless arranged. Sorry no more pets.

25 Jun – 2 Jul

$518 SGD per night

Guest favourite

Flat in Woodstock Valley

4.93 out of 5 average rating, 335 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

UCONN Graduations coming soon, celebrate, relax. Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. Featuring Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy private deck, propane fire pit, gaze at the moon & stars. Cook-Propane grill. Enjoy scenic walks around the lakes. Wake up to amazing sunrises. Pretty flowers, trees surrounding!! Now open-Woodstock Valley Country Store

22–29 Apr

$180 SGD per night

Guest favourite

Home in Sturbridge

4.94 out of 5 average rating, 210 reviews

Lake Front Home Sleeps 6-8 on a private Peninsula!

DIRECT WATER FRONT RENTAL! This breathtaking property is located on it's own PENINSULA! Stunning water views from almost every window. This updated year round charming family home features 3 BR, 2 bath, large living room w/sliders to a wrap around deck, incredible views from a huge, heated sun porch. The large yard with a dock, NEW Patio/Firepit, small private beach area, with kayaks, canoe and a row boat! SUMMER MONTHS: 5 Night minimum Thanksgiving andChristmas Holidays have a 3 night minimum

16–23 Dec

$530 SGD per night

Guest favourite

Guest suite in Thompson

4.98 out of 5 average rating, 114 reviews

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! Room to sleep up to 4, king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

23–30 Aug

$202 SGD per night

Guest favourite

Home in Southbridge

4.94 out of 5 average rating, 306 reviews

Charming Cape--Kid & Dog Friendly 🐾

Old style cape, newly renovated. Lots of vintage charm with new upgrades. Beautiful, 3 bedroom, 1.5 bath & full kitchen. Kitchen is fully stocked with duel kuereg and drip coffee pot & Ninja blender. Beautiful touches throughout to make your stay cozy. EXTRAS INCLUDE : 24-HOUR CHECK-IN / keyless entry FREE COFFEE FREE Oatmeal bar HIGH SPEED WI-FI Pack N Play Glider for nursing/feeding moms! SMART TVs in 2 bedrooms Enjoy a cute stay in quiet neighborhood, 7 minutes from Sturbridge exit (84).

16–23 Dec

$288 SGD per night

Guest favourite

Home in Sturbridge

4.96 out of 5 average rating, 112 reviews

LAKE Retreat! Lakefront Home with Amazing Views!

Beautiful lakefront house with great views. Perfect for a relaxing family vacation. 4 Bedrooms, 3.5 baths sleeps 10 comfortably. Paddle-board, kayak, propane grill, fire pit, & corn hole make for awesome lakefront memories! Game room features bubble boy hockey, board games, & puzzles for rainy day fun! Sturbridge is known for it's locally owned restaurants, breweries, & wedding venues. Get away from it all, but still be close driving proximity to Boston, Worcester, Springfield MA, & CT!

7–14 Jul

$1,404 SGD per night

Guest favourite

Bungalow in Wales

4.9 out of 5 average rating, 184 reviews

Cozy Woodland Bungalow

Relax at our rustic and cozy woodland bungalow for your next trip to Central/Western Mass. Located on a dead end paved road surrounded by acres of woods and farm land, the bungalow is the perfect place to sip your coffee on the porch while enjoying all nature has to offer. Internet access is now available for your convenience. Close to restaurants, microbreweries, and Old Sturbridge Village. Easy access to Route 84 or Route 19, six miles from Brimfield and eight miles from Sturbridge.

12–17 Jun

$195 SGD per night

Guest favourite

Guest suite in Warren

4.95 out of 5 average rating, 265 reviews

Craig's Cove

Craig's Cove is a two-room apartment (in my finished basement) with a farmhouse industrial motif and is in close proximity to Sturbridge, wineries, micro-brews such as Lost Towns Brewing, and beautiful scenery. Guests will be provided with one off-street parking space, private entry, bedroom with queen-size bed, full bathroom, TV with Netflix & Amazon Prime, free wifi, coffee, kitchenette with sink, microwave, fridge, toaster oven, hot plate (no full size stove), and patio with pergola.

16–23 Sep

$97 SGD per night

Guest favourite

Flat in Brimfield

4.98 out of 5 average rating, 138 reviews

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the convenience of a convenience store, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

21–28 Dec

$204 SGD per night