
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.

Cozy Little Cottage
Small comfortable place close to Lime Rock Park and Ski Butternut. It has 3 available bedrooms including one master with full bath. Lots of great restaurants in the area and places to hike or take out your canoe or kayak. Nice private backyard. There is a small fish pool to enjoy. I do have cameras pointing at the front door and back door to see when guests arrive and when they leave. Please don't try and sneak in extra guests you didn't intend to pay for. I've has these issues before. Welcome!

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.

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.

Adorable Apartment - Near Emma Willard, RPI, Troy
Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

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!

Historic Hudson Hideaway
Historic Hudson Hideaway is the first floor of our 1840s home furnished with a mix of modern finds, antique textiles, and luxury linens. The suite has an abundance of natural light and is ideal for those looking for privacy and retreat while being conveniently located a block from Hudson's Amtrak station, and steps to Warren Street shops, restaurants, bars, and arts. City of Hudson Lodging Licensee #1168
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

Lxry Est HeatedPool Hottb Views

Explore the Woodland Areas at Circa 1804 Farmhouse

Rustic Farmhouse Meets Chic!

Jenny’s Folk Art Museum

Elegant Designer Country Home

Upland Meadow Retreat - 3 bedrooms/2 baths
Apartment rentals with breakfast

Suite 23 - Spacious Sunny 2-BR with Mountain view

Private Hudson pied-à-terre; blocks from Amtrak

Cozy Albany Room Next to downtown W/breakfast

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

Comfortable Stay 2

Downtown Albany 2 Bedroom + Workstation @ The Mark

A Sacred Place

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Bed and breakfast rentals with breakfast

The Smithfield Room

Charming Eyebrow Colonial North Chatham, NY

Maple House, Birch Room

Brick Row House in the Woods, private 2nd floor

C1 Carriage House at Blackberry River Inn

Sheffield Lodge - Ramblewood Master

Hospitality in the Berkshire Woods

QUEEN ROOM Bed&Breakfast private bath
Quick stats about holiday rentals with breakfast included in Stockbridge

Total holiday rentals
Explore 20 holiday rentals in Stockbridge

Nightly prices starting at
Stockbridge holiday rentals start at € 129 per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

Holiday rentals with a pool
10 properties feature pools

Wifi availability
20 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
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- Rentals with a fireplace Stockbridge
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- Rentals with breakfast Berkshire County
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- Rentals with breakfast United States
- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Windham Mountain
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Bushnell Park
- Taconic State Park
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Mount Sugarloaf State Reservation
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Talcott Mountain State Park
- Mount Tom State Reservation
- Hartford Golf Club
- Hunter Mountain Resort
- Opus 40
- Mohawk Mountain Ski Area




