Photo by Jennifer LaFountain

Wilbraham Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Wilbraham holiday rentals

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (14)
"Very nice country stay. "
United States
michael C.
The price is NZ$489
includes taxes & fees
3 Jan - 4 Jan 2026
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (30)
"Great host- fun property!"
United States
Mary F.
The price is NZ$442
includes taxes & fees
5 Jan - 6 Jan 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is NZ$583
includes taxes & fees
4 Jan - 5 Jan 2026
Trainmaster's Inn - Caboose

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
2.0 star property
Ware
9.8 out of 10, Exceptional, (7)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is NZ$277
includes taxes & fees
1 Jan - 2 Jan 2026
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (29)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is NZ$456
includes taxes & fees
7 Jan - 8 Jan 2026
Treehouse - Countryside - Farm Animals - Fire Pit

Apartment in town center #1

Apartment in town center #1
West Brookfield
8.8 out of 10, Excellent, (26)
"Clean place and was well suited for what we needed"
United States
Chris
The price is NZ$517
includes taxes & fees
6 Jan - 7 Jan 2026
Apartment in town center #1

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
2.0 star property
Chicopee
10.0 out of 10, Exceptional, (1)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is NZ$584
includes taxes & fees
5 Jan - 6 Jan 2026
Welcoming 3-bedroom house- Gardner home

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
9.2 out of 10, Wonderful, (13)
"For the most part everything was great!"
United States
Gabriel M.
The price is NZ$553
includes taxes & fees
9 Jan - 10 Jan 2026
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Welcome to Honey Spot!

Welcome to Honey Spot!
Pine Point
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is NZ$508
includes taxes & fees
5 Jan - 6 Jan 2026
Welcome to Honey Spot!

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.4 out of 10, Exceptional, (20)
"Beautiful location. Great communication with host who continually checked in with us. Home had everything we needed to host my daughter and her friends for a great dinner for UCONN family weekend. Will definitely be back! "
United States
Michelle L.
The price is NZ$503
includes taxes & fees
1 Jan - 2 Jan 2026
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Tiny Home with AC and WiFi in lovely Ludlow

Tiny Home with AC and WiFi in lovely Ludlow
Ludlow
8.2 out of 10, Very good, (10)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
United States
Matthew H.
The price is NZ$258
includes taxes & fees
13 Jan - 14 Jan 2026
Tiny Home with AC and WiFi in lovely Ludlow

Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.0 out of 10, Wonderful, (29)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
The price is NZ$517
includes taxes & fees
7 Jan - 8 Jan 2026
Spacious Massachusetts Apartment #2

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (13)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
United States
Eric W.
The price is NZ$554
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Home in Holyoke with 3 bedrooms

The Serene Skyway Retreat

The Serene Skyway Retreat
Windsor Locks
9.0 out of 10, Wonderful, (12)
"Pretty house. Great host. Enjoyable stay. Will definitely consider renting it out again, if the opportunity arises.."
United States
Apex A.
The price is NZ$471
includes taxes & fees
19 Jan - 20 Jan 2026
The Serene Skyway Retreat

Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Spacious 4-bedroom condo with AC and WiFi in charming Enfield
Enfield
10.0 out of 10, Exceptional, (2)
"I had a family event in the area and needed a place for 8 people that was of better value than hotel rooms. This location was the perfect option."
United States
Logan M.
Spacious 4-bedroom condo with AC and WiFi in charming Enfield

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.0 out of 10, Wonderful, (26)
"Loved the views of the lake and the decor. "
United States
Beth L.
The price is NZ$546
includes taxes & fees
8 Jan - 9 Jan 2026
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
Charming Chicopee Getaway

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC
Boston Road
9.0 out of 10, Wonderful, (10)
"Great stay"
United States
Angelina O.
The price is NZ$554
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 3-bedroom Duplex2 in beautiful Springfield with WiFi, central AC

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
2.0 star property
South Windsor
The price is NZ$187
includes taxes & fees
23 Jan - 24 Jan 2026
Entire guest suite in South Windsor, Connecticut

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
2.0 star property
Brimfield
The price is NZ$308
includes taxes & fees
4 Jan - 5 Jan 2026
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Wilbraham Hotel Reviews

Find out more about Wilbraham

Everything you need to know about Wilbraham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wilbraham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wilbraham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wilbraham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wilbraham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wilbraham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wilbraham holiday rentals we have selected for you start as low as NZ$277 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wilbraham rentals

At Expedia, we put the best Wilbraham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wilbraham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wilbraham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wilbraham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Wilbraham?

Yes, there are holiday rentals close to the most popular sights in Wilbraham, or you can select a more secluded option if you're looking for a relaxing stay. Wilbraham is known for its shopping and restaurants.

What are some of the best holiday rentals that Wilbraham has to offer?

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: This holiday home rental outside of Wilbraham is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Wilbraham?

While exploring the area, visit family-friendly sights like Zoo in Forest Park and Education Center, or get outside and enjoy nature at Crane Hill Disc Golf Course. Red Bridge State Park and Lake Lorraine State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Wilbraham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wilbraham. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.