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Compare 22 Apartments in Winchendon with updated reviews, rates, and availability.

Relaxing Retreat
Corporate apartment entrance is at the bottom right of the main house

Relaxing Retreat

9.8 out of 10, Exceptional, (25)
"Very nice place to stay. We enjoyed the games available in the closet. The grandson enjoyed the weight and treadmill area. "
Relaxing Retreat
The Covey House Retreat with InfraRed Sauna
Room

The Covey House Retreat with InfraRed Sauna

10.0 out of 10, Exceptional, (3)
"We had an amazing stay, your place is awesome!"
The Covey House Retreat with InfraRed Sauna
Lakefront Orange Vacation Rental - Pet Friendly!
Orange Vacation Rental | 1BR | 1BA | 902 Sq Ft | Access Only By Stairs

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (11)
"Great host communication, everything we needed, unexpected extras (like dog treats), and a beautiful view. Would gladly stay again!"
Lakefront Orange Vacation Rental - Pet Friendly!
Enjoy the country life!
Exterior

Enjoy the country life!

10.0 out of 10, Exceptional, (15)
"We just had an absolutely wonderful weekend stay at the apartment at Sweet Brier Farm! It was quiet, relaxing, comfortable, and well-equipped. We met the adorable farm animals, went in the hot tub, and had two AMAZING homemade breakfasts in the main house. Helen and Keith were so kind and made sure we promptly had everything we needed! We will definitely be staying here again!!!"
Enjoy the country life!
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
Leominster Vacation Rental | 1BR | 1BA | Stairs Required | 900 Sq Ft

Cozy Getaway - 10 Miles to Mount Wachusett Skiing!

10.0 out of 10, Exceptional, (10)
"Nice stay. Kind owner who helped us find the right door when we arrived after dark and hadn’t thoroughly read the instructions. So kind!"
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
Stunning brand new 2 bedroom Loft amidst nature
Living room

Stunning brand new 2 bedroom Loft amidst nature

10.0 out of 10, Exceptional, (16)
"Place was great! Roomy, comfortable, we felt so welcome! Took my dog for a nice walk around the area in the morning and the country roads were safe and well maintained for a walk. "
Stunning brand new 2 bedroom Loft amidst nature
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

9.4 out of 10, Exceptional, (9)
"we were staying in the area for hiking. the space was clean and exactly as described,host was very kind and helpful, and the location is perfect. town is lovely too."
The price is SAR 282
SAR 591 total
includes taxes & fees
7 Jan - 8 January 2025
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Updated Vintage Apartment < 1/2 Mi to Main St
Keene Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Steps Required for Entry

Updated Vintage Apartment < 1/2 Mi to Main St

10.0 out of 10, Exceptional, (11)
"This property was just as expected and Close to top notch restaurants. Kitchen was well equipped and I was able to bake a few casseroles for our family we were visiting.The area was nice and quiet. Will visit again."
Updated Vintage Apartment < 1/2 Mi to Main St
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
Living area

Cozy Getaway - 10 Miles to Mount Wachusett Skiing!

3.0 star property
Cozy Getaway - 10 Miles to Mount Wachusett Skiing!
Updated Vintage Apartment < 1/2 Mi to Main St
Living area

Updated Vintage Apartment < 1/2 Mi to Main St

3.0 star property
Updated Vintage Apartment < 1/2 Mi to Main St
Charming 3-bedroom - 10 miles to Wachusett Mountain Ski Area!!
Room

Charming 3-bedroom - 10 miles to Wachusett Mountain Ski Area!!

Charming 3-bedroom - 10 miles to Wachusett Mountain Ski Area!!
Entire private apartment suite in home with own entrance, views and private gym.
Guest suite entrance and patio area with outdoor grill.

Entire private apartment suite in home with own entrance, views and private gym.

The price is SAR 1,033
SAR 1,508 total
includes taxes & fees
24 Dec - 25 Dec
Entire private apartment suite in home with own entrance, views and private gym.
Cozy side-by-side 1 bed 1 bath Apartment - Relaxing Getaway
Room

Cozy side-by-side 1 bed 1 bath Apartment - Relaxing Getaway

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great to visit to our old haunts - stationed at Fort Devans 20+ years ago... Enjoyed staying at the property - nice and quiet - great sleeping on a very comfortable bed. Nice shower and amenities. Thanks!"
The price is SAR 413
SAR 898 total
includes taxes & fees
6 Jan - 7 January 2025
Cozy side-by-side 1 bed 1 bath Apartment - Relaxing Getaway
Barre Common Overlook
Exterior

Barre Common Overlook

6.0 out of 10, (1)
Barre Common Overlook
Entire Rental unit 5 bed 1.5 bath
Room

Entire Rental unit 5 bed 1.5 bath

Entire Rental unit 5 bed 1.5 bath
Remodeled One bedroom Apto with beautiful View
Interior

Remodeled One bedroom Apto with beautiful View

2.0 out of 10, (1)
"The place is not set up to sleep 4 people."
Remodeled One bedroom Apto with beautiful View
Relax peacefully in Gardner Ma, near Mt Wachusett
Private kitchen

Relax peacefully in Gardner Ma, near Mt Wachusett

Relax peacefully in Gardner Ma, near Mt Wachusett
Driving distance to Wachusett Mountain, Boston, Wocester
Private kitchen

Driving distance to Wachusett Mountain, Boston, Wocester

Driving distance to Wachusett Mountain, Boston, Wocester
Night stay 2 bedroom and bathroom
Dining

Night stay 2 bedroom and bathroom

Night stay 2 bedroom and bathroom
Great looking Private bedroom with a queen size bed
Room

Great looking Private bedroom with a queen size bed

Great looking Private bedroom with a queen size bed
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.
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Other property types in Winchendon

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Exterior

VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

10.0 out of 10, Exceptional, (4)
"This property was great. Wonderfully modern lake front home. Recommend renting the pontoon to fish for larger fish. Kayaks, Paddleboards, great restaurants and sauna. Picture perfect scenery. "
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
Pool

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

10.0 out of 10, Exceptional, (2)
"Stunning property, we had the best time for our annual friendsgiving. The kids loved the backyard and the two kitchens was awesome! "
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
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.

Frequently asked questions

What's it like to stay at an apartment in Winchendon?
You’ll find 8 lodging options in Winchendon. Though there aren’t many apartments, we can help you search for similar accommodations. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. You can even filter by similar properties such as vacation homes, condos, or cabins.
Are you thinking about an apartment for your stay?
Often offering more space than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for solo travelers who want to stay in at night and plan out their next day.
What's the best apartment for my stay in Winchendon?
Below are some of the more popular apartments in the area: Relaxing Retreat: Situated in Westminster, 12 mi/19.3 km from the heart of Winchendon. Lakefront Orange Vacation Rental - Pet Friendly!: It’s situated in Orange, 10.2 mi/16.4 km away. Includes fireplaces. The Covey House Retreat with InfraRed Sauna: Located 8.3 mi/13.4 km away in Fitzwilliam. Free WiFi and Smart TVs are included. Access to a fitness center is available on site. Enjoy the country life!: It’s located in Lyndeborough, 18.7 mi/30.1 km from Winchendon. Includes free WiFi, sofa beds, and Smart TVs.
What will the weather be like when I travel to Winchendon?
Though weather is just one factor, it can really affect your travel plans, especially when you are planning a longer stay in Winchendon. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchendon are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What are the must-see places to visit in Winchendon?
Lake Dennison State Recreation Area and Hyde Park are a couple of scenic spots to enjoy the outdoors, whereas The Robinson-Broadhurst Foundation Performing Arts Ampitheater is one of the cultural attractions. While here, Birch Hill Wildlife Management Area and Wendall P. Clark Memorial are other places worth a visit.
What's the best way to get to and around Winchendon?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Nashua, NH (ASH-Nashua Municipal), which is located 28 mi (45.1 km) from the heart of the city. You can also search for flights into Worcester, MA (ORH-Worcester Regional), which is 30.1 mi (48.5 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.