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Vacation rentals in Holyoke

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Top-rated vacation rentals in Holyoke

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Cottage in Becket

4.94 out of 5 average rating, 176 reviews

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Home in Bloomfield

4.95 out of 5 average rating, 111 reviews

Spacious Charming New England Cape

Beautiful, relaxing area across from woods near Wintonbury Hills Golf course. Neighborhood setting and on a private corner lot. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails too! Close to Ski Sundown, Mt Tom, MGM Casino, tons of golf courses, beaches.

Guest suite in Winchester

4.95 out of 5 average rating, 123 reviews

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! The Holidays have Arrived! Book the Season Early!!! Modern 2-bedroom private bath suite in the foothills of the Berkshires! Views of Highland Lake from your private sundeck. Moon and star gazing by night. ART: The studio of International Folk Artist Cheryl Bartley is on lower level and available for creatives. Art studio use for small fee. Free studio tour! POLICY: We follow all Airbnb policies & State of CT COVID cleaning guidelines.

Home in Becket

4.88 out of 5 average rating, 329 reviews

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Home in Chester

4.96 out of 5 average rating, 341 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Cottage in Litchfield

4.88 out of 5 average rating, 312 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area

Home in Winsted

4.99 out of 5 average rating, 110 reviews

Cheerful 2 Bedroom Home at Highland Lake

Welcome to the Uncorked Cottage, a fun and relaxing space for you and your family to retreat to. Comfort meets style in this updated home with a cozy remote gas fireplace, 55” smart TV and high speed WiFi. The kitchen is fully equipped cook up your favorite recipes. Located across the street from Highland lake and walking distance to Resha Beach. Just minutes from downtown where you’ll find restaurants and activities for all. Just a short drive to ski mountains.

Bungalow in Longmeadow

4.76 out of 5 average rating, 202 reviews

Artist Longmeadow 3bdrmHOUSE with OUTDOOR SAUNA

Welcome to my sanctuary of creativity, culture, and connection in Longmeadow, where hospitality is my way of sharing love, joy, and a glimpse into my Haitian heritage. This inviting space is designed to feel like home while inspiring your stay. Relax in the outdoor sauna, fire up the BBQ, or simply unwind in the quiet backyard. Across from a serene park, this is a retreat to recharge, connect, and create lasting memories. Self-check-in makes arriving a breeze.

Home in Otis

4.92 out of 5 average rating, 147 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Cottage in Becket

4.94 out of 5 average rating, 270 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

Home in Otis

4.96 out of 5 average rating, 105 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Apartment in Hawley

4.89 out of 5 average rating, 137 reviews

Green Acres Hawley Upper Studio (Bonus Room)

This space is a Large Studio Apartment in the Bonus Room above the Garage of a large log home overlooking Berkshire East Mountain Resort. Guests have shared access to the hot tub, outdoor tub/shower, deck, fire pit barbecue area and laundry facilities. You'll have sole access to the bonus room, deck & grill and full private bath. Space is comfy and charming, accessible from a private staircase or spiral into the main house's entrance hall.

Vacation rentals for every style

Get the amount of space that is right for you

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Convenient locations with everyday essentials

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Hotels

Stylish accommodations and amenities

Popular amenities for Holyoke vacation rentals

Free parking on premises

Air conditioning

Stay near Holyoke's top sights

Mount Tom State Reservation41 locals recommend

Holyoke Mall31 locals recommend

Coco and The Cellar Bar28 locals recommend

Small Oven Bakery25 locals recommend

Luthier's Co-Op19 locals recommend

Abandoned Building Brewery19 locals recommend

Other great vacation rentals in Holyoke

Home in Belchertown

4.98 out of 5 average rating, 51 reviews

Moonstone n' Lucy's Lake House – romantic, serene

Home in Lee

4.91 out of 5 average rating, 11 reviews

Modern Retreat on Goose Pond

Home in Otis

4.93 out of 5 average rating, 14 reviews

Spacious Lake Front Home

Cabin in Sandisfield

4.99 out of 5 average rating, 98 reviews

Berkshires Cabin in Woods with Mountain Views

Guest suite in Granby

4.91 out of 5 average rating, 143 reviews

Whole place,staycation,3 bedrooms, spacious area

Home in Becket

4.95 out of 5 average rating, 61 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

Guest suite in Easthampton

4.91 out of 5 average rating, 247 reviews

The Floating Library: private hiker's hideaway

Home in Ashford

4.83 out of 5 average rating, 78 reviews

Amazing lake home w/ amenities.

Quick stats about vacation rentals in Holyoke

Total rentals
80 properties
Nightly prices starting at
G$8,359 GYD before taxes and fees
Total number of reviews
5.7K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Are there pet-friendly vacation rentals in Holyoke?
Four-legged friends are welcome in Holyoke. Choose from more than 20 vacation rentals for guests traveling with pets.
Where should I stay in Holyoke?
Make yourself at home in Holyoke by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Rock Valley, over 10 vacation rentals in Aldenville, and over 30 vacation rentals in Springdale.
Are there family-friendly vacation rentals in Holyoke?
Holyoke has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Holyoke?
Experience the best of Holyoke with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do private suite rentals in Holyoke have wifi?
Absolutely! We offer over 10 private suite rentals with wifi in Holyoke. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Private Suite Rentals in Holyoke?
Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Holyoke have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Holyoke. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Holyoke have air conditioning?
Absolutely! We offer over 10 private suite rentals with air conditioning in Holyoke. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Holyoke have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Holyoke. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Holyoke?
Yes! Work meets play with ease at over 50 vacation rentals in Holyoke featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore