
Holiday rentals with breakfast in Stockbridge
Find and book unique rentals with breakfast on Airbnb
Top-rated rentals 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.

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.

Netherwood - North Adams Guest House with Views
Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

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.

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 !

Downtown Albany 2 Bedroom + Workstation @ The Mark
Charming 2 Bedroom + Workstation apartment in Downtown Albany. Centrally located and easy walking! NFL Blitz Arcade Game. Pets allowed! 2nd FL apartment with an elevator on site! Enjoy hardwood floors, a custom kitchen, soaking bathtub, and central AC. Featuring a King Bed, Queen bed, pull-out couch, workstation with monitor, and free WiFi. Includes access to a shared washer/dryer. For long term stays over 1 month, a monthly parking space will be included. Parking garage close by.

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.

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.

Rustic Farmhouse Meets Chic!
This stylish and spacious place to stay is perfect for family trips! 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.

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!

Garden Paradise minutes from Hudson
We are just a 10 minute drive from Hudson's bustling Warren Street in the historic hamlet of Claverack. We live on the property, but our guesthouse is separate and private. It's all surrounded by our 2 1/2 acre garden, which is our passion as well as our profession. We've recently adapted a 2 year old standard poodle named Nora. She is a very shy little girl, and will win your heart. We are sorry, but we do not accept pets or children under 12.

Private Studio Close to Downtown Rhinebeck
This modern studio apartment is ideal for a weekend retreat or remote working base. Just 17 minutes from Omega, we offer a Queen-size bed, free WiFi, and a Smart TV. The fully-equipped kitchenette and work/eating bar make meal prep and productivity easy. The bathroom features a rain shower head and Bluetooth speaker. With its own entrance and ample street parking, it ensures privacy and convenience. Give it a try – you won’t be disappointed!
Popular amenities for rentals with breakfast in Stockbridge
House rentals with breakfast

All-Season Berkshires Escape: Ski, Hike, Swim

Secluded Hudson mid-century - pool & hot tub

NEW: Chic Colonial - Family, Fun, Food & Forays!

Stylish farmhouse, heated pool, 3 mins from Hudson

Explore the Woodland Areas at Circa 1804 Farmhouse

Jenny’s Folk Art Museum

Light-filled Lake House in Goshen

Elegant Designer Country Home
Apartment rentals with breakfast

Rural retreat in Colebrook CT

Private Hudson pied-à-terre; blocks from Amtrak

Limbe Guest House

Maple House, Oak Room

Albany Cozy Room Next to downtown W/breakfast

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

Comfortable Stay 2

A Sacred Place
Bed and breakfast rentals with breakfast

Mountain View Queen Suite w pool and patio

The Smithfield Room

Charming Eyebrow Colonial North Chatham, NY

Norton Hill BnB

Brick Row House in the Woods, private 2nd floor

The Sara Tracy House, Whitman Room

C1 Carriage House at Blackberry River Inn

Hospitality in the Berkshire Woods
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 $165 SGD per night before taxes and fees

Verified guest reviews
Over 360 verified reviews to help you choose

Holiday rentals with a pool
10 properties feature pools

Wifi availability
30 of Stockbridge holiday rentals include wifi 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
Destinations to explore
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- House rentals Stockbridge
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- Rentals with a fireplace Stockbridge
- Rentals with a hot tub Stockbridge
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- Hotel rooms Stockbridge
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- Rentals with breakfast Berkshire County
- Rentals with breakfast Massachusetts
- Rentals with breakfast United States
- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Thacher State Park
- Windham Mountain
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Butternut Ski Area and Tubing Center
- Kent Falls State Park
- Zoom Flume
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Ski Sundown
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Millbrook Vineyards & Winery
- Poets' Walk Park
- New York State Museum




