Glendale holiday lettings

We found 524 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Glendale that are perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Glendale

Showing deals for:1 Jan - 8 Jan

Outdoor spa tub
Exterior
Living area
Interior
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
£3,793
for 7 nights, 1 home
£542 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Second Floor Bedroom #3 - Master Suite
(see floor plans as reference)
Interior
Exterior
Living room from back staircase
Exceptional
(53 reviews)

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington

8% off
£5,787
for 7 nights, 1 home
£827 per night
includes taxes & fees
Beautiful Berkshire Farm House on 160+ Acres
Private kitchen
Terrace/patio
Pool
Property grounds
Exceptional
(5 reviews)

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale

7% off
£6,453
for 7 nights, 1 home
£922 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Exterior
Private kitchen
Property grounds
Terrace/patio
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
£4,035
for 7 nights, 1 home
£576 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Outdoor dining
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
£3,250
for 7 nights, 1 home
£464 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Living Room

Great Barrington Castle house
Front view of home
Great Barrington Castle
Exceptional
(52 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

7% off
£3,632
for 7 nights, 1 home
£519 per night
includes taxes & fees
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Seamless entertaining with the wide open concept, living room -kitchen- patio
After a hard day on the trails or a long day on the town, relax in this oasis
Never miss a thing with this expansive open concept kitchen and living room
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
£3,510
for 7 nights, 1 home
£501 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Back patio with Hot Tub
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Welcome Home!
Exceptional
(8 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
£4,634
for 7 nights, 1 home
£662 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Exterior
Interior
Property grounds
Living area
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
£2,075
for 7 nights, 1 cabin
£296 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Alfresco dining
River view from window
dining area
Blue House side entry from driveway
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

7% off
£2,119
for 7 nights, 1 home
£303 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Living area
Interior
Room
Private kitchen
Exceptional
(62 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
£904
for 7 nights, 1 apartment
£129 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Queen bedroom
Terrace/patio
Property grounds
Screened in porch
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
£2,164
for 7 nights, 1 home
£309 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Outdoor dining
Room
Dining
Private kitchen
Exceptional
(33 reviews)

The Hideaway: Berkshire Home - Village of Egremont

egremont

16% off
£1,982
for 7 nights, 1 home
£283 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Kitchen
Interior
Interior
Property grounds
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
£3,048
for 7 nights, 1 home
£435 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Private kitchen
Outdoor dining
Exterior
Private kitchen
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
£2,152
for 7 nights, 1 home
£307 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Entry and living room
Dining
view into large bathroom
Living Room, wow!
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
£1,937
for 7 nights, 1 apartment
£277 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Private kitchen
Ultimate Relaxation!  The hot tub will be warm and waiting for your arrival
Open floor plan, natural light in a stylish space
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
£2,215
for 7 nights, 1 home
£316 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Exterior
Property grounds
Interior
Interior
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
£1,051
for 7 nights, 1 apartment
£150 per night
includes taxes & fees
The Serendipity Spot
Our hanging egg chair is the most popular seat in the house #Instagram yourself!
Private entry is with the parking in the rear of the house.
Room
Exterior
Exceptional
(24 reviews)

New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

Stockbridge

24% off
£1,422
for 7 nights, 1 apartment
£203 per night
includes taxes & fees
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
Bathroom
Living area
Private kitchen
Room
Exceptional
(7 reviews)

Comfortable, renovated 2 bedroom apartment in historic grist mill.

SOUTH EGREMONT

16% off
£1,421
for 7 nights, 1 apartment
£203 per night
includes taxes & fees
Comfortable, renovated 2 bedroom apartment in historic grist mill.
Gorgeous open concept living room
Private kitchen
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Quarter & Rift sawn white oak floors
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

10% off
£3,746
for 7 nights, 1 apartment
£535 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Glendale getaway

Learn about the unique charm of Glendale with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Glendale

Do you want to find things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Glendale a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Wyndhurst Golf & Club (5.6 mi / 9 km)
  • Ski Butternut (6.6 mi / 10.6 km)
  • Kennedy Park (7.6 mi / 12.2 km)
  • Bousquet Ski Area (9.8 mi / 15.9 km)
  • Catamount Ski Area (10.7 mi / 17.3 km)
  • Otis Ridge (13.1 mi / 21.1 km)

Exploring the natural features in Glendale

Whether you're an outdoor enthusiast or just want to take in the scenery, Glendale is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Naumkeag Museum (1.1 mi / 1.8 km)
  • Berkshire Botanical Garden (1.6 mi / 2.6 km)
  • Stockbridge Bowl (4 mi / 6.5 km)
  • The Mount (4.7 mi / 7.6 km)
  • Housatonic River (5.7 mi / 9.2 km)
  • Housatonic River Walk (5.8 mi / 9.3 km)

Travelling to and around Glendale

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 10.4 mi (16.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Hudson, NY (HCC-Columbia County), which is 19.5 mi (31.3 km) away.

Frequently asked questions

Are there holiday rentals in Glendale?
Yes, there are holiday rentals close to the most popular sights in Glendale, or you can select a more secluded option if you're looking for a relaxing stay.
How many holiday rentals are there in Glendale?
Choose from 3 Expedia holiday rentals in Glendale for a memorable holiday.
What can I see and do in Glendale?
While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Housatonic River. In the wider area, you'll find Norman Rockwell Museum and Naumkeag Museum.
What are holiday rentals like in Glendale?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Glendale. Holiday rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family getaway.