
Holiday rentals with breakfast in Stockbridge
Find and book unique Holiday Accommodation with Breakfast on Airbnb
Quick stats about holiday rentals with breakfast included in Stockbridge

Total holiday rentals
Explore 30 holiday rentals in Stockbridge

Nightly prices starting at
Stockbridge holiday rentals start at $213 AUD per night before taxes and fees

Verified guest reviews
Over 390 verified reviews to help you choose

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
30 of Stockbridge holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Stockbridge rentals

4.6 Average rating
Stockbridge stays receive an average rating of 4.6 out of 5 from guests

Nearby attractions
Stockbridge's top spots, include Norman Rockwell Museum, Naumkeag, and Berkshire Botanical Garden
Top-rated Holiday Accommodation with Breakfast in Stockbridge
Guests agree: These breakfast rentals are highly rated for location, cleanliness and more.

1 bdrm apt in Athens on the Hudson
Come enjoy village life right in the middle of this friendly and vibrant, yet quiet community in your own charmingly appointed 3 room apartment. Explore the Great Northern Catskills with its boating and paddling opportunities, antiquing, local history, art and music. The Thomas Cole House is minutes away in Catskill. Olana is right across the Rip Van Winkle Bridge. If sculpture is your passion, Opus 40 in Saugerties is not to be missed. Winerys abound and be sure not to miss Athens own brewery.
LocationFamilyBackyard

Patchin Mills Quaint Country Cottage
Welcome to your cozy cottage in the bucolic Hudson Valley. Only 90 mi. north of NYC. We welcome small dogs, under 25 lbs. with prior host approval. Sorry, NO CATS. Enjoy biking, hiking, skiing, local culture or just relaxing. 1 mile outside a charming village in farm and horse country, your cottage has a full kitchen/LR, 2 BRS (1 queen, 1 full), bathrm, washer/dryer, deck, patio & yard. Close to colleges, dining & activities. We hope that you will love this corner of the world as much as we do.
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Bright Stockbridge country home, near everything!
Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.
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Spacious, new renovated 1BR in a Victorian mansion
Ultra-prime location on Allen Street, this spacious, recently renovated 1BR apartment is nestled privately within an historic Victorian located on Hudson’s Mansion Row! 3-minute walk to bustling Warren Street and renowned shops and dining. Built in 1865 by Hudson mayor Joshua T. Waterman, the House features an Italianate tower and preserved historic details. It previously operated as the beloved Hudson City Bed & Breakfast for over 35 years, and now under new ownership, as The Waterman House.
LocationFamilyHeating

Suite 23 - Spacious Sunny 2-BR with Mountain view
Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !
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West Main
1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town , pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.
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Elegant Townhouse + 3 Ensuite Baths + Central
3-bedroom new and modern townhouse centrally located with en suite baths in every bedroom (walk-in showers, soaking tub) and a powder room on main floor; chef's kitchen (induction cooktop, convection and speed ovens, built-in refrigerator with ice maker, dishwasher, wine cooler); two living rooms, one with smart tv; silent split-unit heating and cooling; washer/dryer; off-street parking; private decks; garden + grill in back; high speed internet; built-in desks in every bedroom.
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Unique People & Pet-Welcoming Haven
Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662
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Private Hudson pied-à-terre; blocks from Amtrak
Private hideaway on Warren Street--entire floor--in a renovated, historic 18th Century house. Queen bed, en suite bathroom, cozy living area with fridge and coffee maker plus a large private deck with panoramic city and mountain views. Walk to everything, from Basilica to Rivertown. Includes light breakfast with locally baked breads and coffee/tea delivered to your door. (Rate now reflects 4% Hudson lodging tax.) Note: Masks still required in hallways and shop. Thank you.
ValueFamilyKitchen

Charming Guest Suite in the Hudson Valley
Nestled in the heart of the Hudson Valley on a quiet country road, this house features a private, newly renovated space at the back of a unique house built in 1789. Surrounded by trees and nature, it makes for a perfect relaxed setting, with access to your own private deck and back yard. A short walk to enjoy Hunns Lake and close to the Buttercup Sanctuary, Stissing Mountain trails, Pine Plains and Millbrook villages. It’s the ideal retreat for a peaceful country getaway.
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Rustic Farmhouse Meets Chic
This stylish and spacious home is perfect for family trips or small groups! Enjoy your privacy in this completely renovated three bedroom house, with full bathroom, and fully equipped kitchen. Located in the heart of Delmar, within walking distance to restaurants, bars, Stram Center for Integrative Medicine, and less than 10 minutes drive to Downtown Albany, Interstate 87 exit, 12 minutes drive to Albany Medical Center, and 20 minutes from the Albany International airport.
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Relaxing secluded stay with loving social animals.
Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!
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Popular amenities for Stockbridge Holiday Accommodation with Breakfast
Holiday House Rentals with breakfast

Adventure in the woods! The Best
LocationConditionCleanliness

All-Season Berkshires Escape: Ski, Hike, Swim
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Secluded Hudson mid-century - pool & hot tub
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Lake Escape
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Stylish farmhouse, heated pool, 3 mins from Hudson
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Explore the Woodland Areas at Circa 1804 Farmhouse
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Charming Eyebrow Colonial North Chatham, NY
LocationFamilyIndoor spaces

Historic New England with Sunset Views
Hospitality
Apartment rentals with breakfast

Rural retreat in Colebrook CT
ValueLocationSleep quality

'The Baker's Loft' 3BR Flat in Chatham Village, NY
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Downtown Albany 1 Bed + Workstation @ Maiden Lane
LocationValueKitchen

Limbe Guest House
FamilyLocationQuiet

Albany Cozy Room Next to downtown W/breakfast
ValueComfortIndoor spaces

Bright, Charming 3-BR with Garden in Heart of Town
ValueFamilyAmenities

Classic Troy Suite • Free Parking • Near RPI
LocationFamilyHeating

Sky view Retreat, a serene hillside hideaway.
LocationFamilyDecor
Bed and breakfast rentals with breakfast

The Smithfield Room
LocationFamilyBathroom

Norton Hill BnB
FamilyLocationOutdoor spaces

Standard Suite at Shaker Mill Inn
LocationGetting aroundCheck-in

Maple House, Birch Room
FamilyLocationBreakfast

Brick Row House in the Woods, private 2nd floor
ValueLocationAccuracy

Sheffield Lodge - Ramblewood Master
ValueFamilyComfort

C14 Carriage House at Blackberry River Inn
Sleep qualityParkingHiking

Hospitality in the Berkshire Woods
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- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Windham Mountain
- June Farms
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Thacher State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Millbrook Vineyards & Winery
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- University of Massachusetts Amherst
- MVP Arena
- Naumkeag
- New York State Museum
- Poets' Walk Park
- Massachusetts Museum of Contemporary Art





