
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 $226 NZD per night before taxes and fees

Verified guest reviews
Over 380 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.

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.

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.

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.

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 !

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.

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

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.

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.

Bright, Charming 3-BR with Garden in Heart of Town
Charming, spacious, art-filled 1st floor of a Federal-era home on a beautiful, peaceful street. Town center is one-minute's walk from the house. 2 Gbps wi-fi! Full kitchen & buddha garden w/ BBQ. Late check-out available unless other guests are imminent. NB: Nightly price reflects that between ABNB (18.34%) + Hudson (5%), hosts here now pay more than 20% of every bill in taxes. Please also see my other listing, "BOHEMIAN RHAPSODY WITH GARDEN IN THE HEART OF TOWN."

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.
Popular amenities for Stockbridge Holiday Accommodation with Breakfast
Holiday House Rentals with breakfast

Adventure in the woods! The Best

All-Season Berkshires Escape: Ski, Hike, Swim

Secluded Hudson mid-century - pool & hot tub

NEW: Chic Family Home in Boutique Town

Lake Escape

Stylish farmhouse, heated pool, 3 mins from Hudson

Explore the Woodland Areas at Circa 1804 Farmhouse

Historic New England with Sunset Views
Apartment rentals with breakfast

Rural retreat in Colebrook CT

'The Baker's Loft' 3BR Flat in Chatham Village, NY

Downtown Albany 1 Bed + Workstation @ Maiden Lane

Limbe Guest House

Albany Cozy Room Next to downtown W/breakfast

Sky view Retreat, a serene hillside hideaway.

Classic Troy Suite • Free Parking • Near RPI

A Sacred Place
Bed and breakfast rentals with breakfast

The Smithfield Room

Charming Eyebrow Colonial North Chatham, NY

Norton Hill BnB

Standard Suite at Shaker Mill Inn

Maple House, Birch Room

Brick Row House in the Woods, private 2nd floor

C14 Carriage House at Blackberry River Inn

Hospitality in the Berkshire Woods
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Baltimore Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Rentals with a washing machine and dryer Stockbridge
- Rentals with a fire pit Stockbridge
- Rentals with a patio Stockbridge
- Rentals with pools Stockbridge
- Rentals with a fireplace Stockbridge
- Rentals with outdoor seating Stockbridge
- House rentals Stockbridge
- Pet-friendly rentals Stockbridge
- Hotel rooms Stockbridge
- Rentals with beach access Stockbridge
- Fitness-friendly rentals Stockbridge
- Rentals with a hot tub Stockbridge
- Rentals with lake access Stockbridge
- Family-friendly rentals Stockbridge
- Rentals with breakfast Berkshire County
- Rentals with breakfast Massachusetts
- Rentals with breakfast United States
- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- June Farms
- Bash Bish Falls State Park
- Taconic State Park
- Thacher State Park
- Zoom Flume
- Kent Falls State Park
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Ski Sundown
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Millbrook Vineyards & Winery
- University of Massachusetts Amherst
- Norman Rockwell Museum
- Naumkeag
- MVP Arena





