Holiday rentals in Monson

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Monson

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Brimfield

4.88 out of 5 average rating, 206 reviews

Little House Inn - Brimmy - Private Home

NO CLEANING FEES - NO CHORE LIST. Relax with the family at our Little House. Create your own fantasy in our Pirate/Castle-themed bedroom perfect for kids of all ages. Our home is kid and pet friendly. We provide a portable crate for pet, food bowls, a kitty litter box and large back yard for our furry guests . Enjoy our home's private backyard that includes a babbling brook & fire pit. Whip up a meal in our full kitchen then sit back and relax with the family or friends. Check out our guidebook for places to eat & sightseeing opportunities.

Guest favourite

Guest suite in Springfield

4.92 out of 5 average rating, 139 reviews

Luxury studio apartment-walkout basement

Located in a quiet neighbor hood in Sixteen acres springfield, this luxury studio was created with you in mind! The bathroom is loaded with spa like amenities include a rain head shower, and heated floors. Located 7 minutes from Western New England University, 13 minutes from Springfield College and American International College. Also conveniently close to many restaurants and shopping amenities. The perfect stay for a traveling nurse or a business trip or even as the home base for a getaway!

Guest favourite

Farm stay in Hampden

4.91 out of 5 average rating, 34 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.

Guest favourite

Flat in Brimfield

4.98 out of 5 average rating, 172 reviews

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the ease of a convenience store, gas station, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

Top guest favourite

Flat in Wilbraham

4.98 out of 5 average rating, 116 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, 41 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, 100 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, 451 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Guest favourite

Flat in Stafford

4.94 out of 5 average rating, 156 reviews

Modern Industrial Apartment with rooftop access

* Modern industrial apartment with rooftop access. * Nestled in an old Mill Building/Artist Community. * Centrally located between Boston and NYC. * 15 mins to UConn, 20 mins to Brimfield Antique Show. * 40 mins to MGM Casino in Springfield, MA. * Walk to restaurants, boutiques, parks, and events. * On-site Yoga, Dance, Recording Studio & Vintage Shop.

Guest favourite

Flat in Brimfield

4.91 out of 5 average rating, 143 reviews

Lovely one bedroom apartment with own entrance

Kick back and relax in this calm, stylish space. Newly remodeled space on the ground floor of my home. Separate entrance. Close to area breweries, Old Sturbridge, Brimfield Antique Show and the new Thirteenth World Fright Park. Easy ride down Rt 20 to Sturbridge or Palmer Mass Pike exits.