Holiday rentals in Wilbraham

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Top-rated holiday rentals in Wilbraham

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

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Superhost

Cabin in Wilbraham

4.7 out of 5 average rating, 33 reviews

1925 3BR Lake Cottage+Fireplace+Detached Office

Private, antique, tranquil Lake getaway. Perfect for the business traveler or family looking at staying in Western Massachusetts ; Right off of Rt20 in Wilbraham, on Nine Mile Lake, 9 miles from Springfield, minutes to Wilbraham Monson Academy , AIC and Western New England University, and 45min to downtown Worcester. If you are looking for a antique cabin lake experience with updates but maintains the older feel- this is it - fully renovated, but vintage 1920's Cabin built by my Irish GFather.

Top guest favourite

Campervan/Motorhome in Wilbraham

4.97 out of 5 average rating, 233 reviews

The Waddle on Inn

Welcome to The Waddle On Inn! Unique small farm experience meets luxury glamping and a serene paradise. We have created a farm getaway with a luxury 5th wheel with all the familiar comforts of home including wifi, smart TV, a screened in pavilion for you to enjoy your meals, our hilarious flock of ducks and goats for your entertainment! There are even fresh duck eggs for purchase as a take home souvenir! Relax, unwind, and Waddle On Inn! *Sunday check in time is 5pm all other days is 4pm*

Guest favourite

Farm stay in Hampden

4.92 out of 5 average rating, 37 reviews

The Hampden House

Escape to serenity at our small farm, nestled in peaceful Hampden, outside Springfield. With its open and roomy layout, this charming property provides ample space for families to relax and unwind together. The fully fenced yard is perfect for kids and pets to run and play safely. Whether you're seeking a relaxing retreat or an adventure-filled escape, our farm has something for everyone. Book your stay and experience the serenity of country living, perfect for creating family memories.

Top guest favourite

Flat in Wilbraham

4.98 out of 5 average rating, 117 reviews

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Guest favourite

Guest house in Enfield

4.95 out of 5 average rating, 44 reviews

Close BDL AirPort & SixFlags Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat.

Superhost

Townhouse in Springfield

4.78 out of 5 average rating, 103 reviews

2 bedroom Glamorous Waterfront Home

Convenient home by the lakeside. Close to all amenities, beaches, plaza and mall! Local attractions to consider: Forest park, The amazing world of Dr Seuss, Springfield Amory National Historic Site, Zoo in Forest Park and education center, MGM casino, Titanic museum, Six Flags, Basketball hall of fame, and many more. There is a path to the pond. Note: Unfortunately, there is no private beach.

Guest favourite

Treehouse in Willington

4.91 out of 5 average rating, 456 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Guest favourite

Tiny home in Granby

5 out of 5 average rating, 42 reviews

Tiny House on Big, Pet-Friendly Farm

Cozy, clean 350sf tiny house on gorgeous farm. Enjoy the serenity of rural life, while being 15 minutes away from downtown Springfield and MGM Casino and 5-15 minutes away from all the local universities. Pet-friendly with a private yard and view you could look at all day. Tempurpedic queen bed, smart TV and lots of other amenities!

Guest favourite

Home in Springfield

5 out of 5 average rating, 12 reviews

VDM Property!

This luxurious home with a spacious yard offers a perfect blend of opulence and warmth. As you enter the door, you're greeted by tasteful decor and soft ambient lighting. The interior boasts a seamless flow of unique spaces, each exuding its own charm and character. Enjoy a stylish experience at this centrally-located place.