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Cruises By Owner - Vacation Rentals in Pittsford

Lakeside Cruise, Bird Lake, Osseo MI From US $100
         

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Boat Rental
Lakeside Cruise, Bird Lake, Osseo MI
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  • Child Friendly

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Luxury Places to Stay in Pittsford

Over 102+ Luxury Places to Stay in or Near Pittsford
Rustic crafted Cowboy Town complete with everything needed for a weekend retreat From US $594
         

New
Resort
Rustic crafted Cowboy Town complete with everything needed for a weekend retreat
  • Parking
  • Pool
  • Designated Smoking Area

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4 Mi to Dtwn: Spacious Family Cabin in Jonesville! From US $470
         

9.8 (6 Reviews)
Cabin
4 Mi to Dtwn: Spacious Family Cabin in Jonesville!
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  • Parking
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4 Mi to Dtwn Spacious Family Cabin in Jonesville! From US $464
         

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House
4 Mi to Dtwn Spacious Family Cabin in Jonesville!
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Devils Lake 5 bedroom Home Nestled In The Beautiful Village Of Manitou Beach, Mi From US $437
         

9.6 (13 Reviews)
House
Devils Lake 5 bedroom Home Nestled In The Beautiful Village Of Manitou Beach, Mi
  • Air Conditioner
  • Parking
  • TV

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Lakefront home- all amenities & beautiful view. Updated beds/carpet/furniture From US $426
         

9.8 (44 Reviews)
Cottage
Lakefront home- all amenities & beautiful view. Updated beds/carpet/furniture
  • Air Conditioner
  • Parking
  • TV

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Cozy Hillsdale Home about 1 Mi to Baw Beese Lake! From US $422
         

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8.0 (1 Review)
House
Cozy Hillsdale Home about 1 Mi to Baw Beese Lake!
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  • Accessibility
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Charming 3BR Waterfront Cottage on Devil's Lake with 90 Feet of Lakefront Living From US $394
         

9.6 (32 Reviews)
Cottage
Charming 3BR Waterfront Cottage on Devil's Lake with 90 Feet of Lakefront Living
  • Air Conditioner
  • Parking
  • TV

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Cozy home in historic Hillsdale From US $353
         

9.6 (31 Reviews)
House
Cozy home in historic Hillsdale
  • Air Conditioner
  • Parking
  • TV

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Top-Rated Vacation Rentals with a Pool in Pittsford

Over 5+ Top-Rated Vacation Rentals with a Pool in or Near Pittsford
Hillsdale College Dow Hotel and Conference Center From US $227
         

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9.6 (204 Reviews)
Hotel
Hillsdale College Dow Hotel and Conference Center
  • Air Conditioner
  • Parking
  • Pool

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Hillsdale College Dow Hotel and Conference Center From US $219
         

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9.6 (118 Reviews)
Hotel
Hillsdale College Dow Hotel and Conference Center
  • Air Conditioner
  • Parking
  • Pool

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Days Inn by Wyndham Hillsdale From US $112
         

7.4 (805 Reviews)
Hotel
Days Inn by Wyndham Hillsdale
  • Air Conditioner
  • Parking
  • Pool

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Villa Vellucci : YOUR OWN PRIVATE RETREAT w/Indoor Heated Pool and more From US $339
         

10.0 (104 Reviews)
Villa
Villa Vellucci : YOUR OWN PRIVATE RETREAT w/Indoor Heated Pool and more
  • Air Conditioner
  • Parking
  • Pool

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Country farmhouse close to Hillsdale College. From US $400
         

8.0 (1 Review)
Other
Country farmhouse close to Hillsdale College.
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Pittsford

Over 21+ Pet-Friendly Vacation Rentals in or Near Pittsford
BEAUTIFUL LAKEFRONT COTTAGE! ☀️🧡 KAYAKS! CLEAR SANDY BOTTOM From US $283
         

10.0 (38 Reviews)
Cottage
BEAUTIFUL LAKEFRONT COTTAGE! ☀️🧡 KAYAKS! CLEAR SANDY BOTTOM
  • Air Conditioner
  • Parking
  • Pet Friendly

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Family-Owned 3 Bedroom with all Amenities including Coffee Machine, Parking, Fast WiFi From US $135
         

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9.4 (17 Reviews)
House
Family-Owned 3 Bedroom with all Amenities including Coffee Machine, Parking, Fast WiFi
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lost Nations Cowboy Town Bear Cabin From US $106
         

10.0 (3 Reviews)
Cabin
Lost Nations Cowboy Town Bear Cabin
  • Parking
  • Pet Friendly
  • Designated Smoking Area

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Lost Nations Cowboy Town Mining Company Cabin From US $93
         

9.4 (8 Reviews)
Cabin
Lost Nations Cowboy Town Mining Company Cabin
  • Parking
  • Pet Friendly
  • Designated Smoking Area

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Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed From US $84
         

9.2 (45 Reviews)
Apartment
Heart of Hillsdale 1 Bdrm, Work,Cook, Relax Wifi Downtown Apartment Queen Bed
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lost Nations Cowboy Town Riverside Cabin From US $106
         

8.8 (9 Reviews)
Cabin
Lost Nations Cowboy Town Riverside Cabin
  • Parking
  • Pet Friendly
  • Designated Smoking Area

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Heart of Hillsdale Downtown Office/Kitchen/Two Beds/Close to Everything From US $84
         

8.6 (34 Reviews)
Apartment
Heart of Hillsdale Downtown Office/Kitchen/Two Beds/Close to Everything
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bears Den Lake Access Retreat, Family/Pet Friendly – Your Peaceful Escape From US $189
         

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Cabin
Bears Den Lake Access Retreat, Family/Pet Friendly – Your Peaceful Escape
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Pittsford

Over 11+ Large Vacation Homes & Villas in or Near Pittsford
Cozy Hillsdale Home ~ 1 Mi to Baw Beese Lake! From US $274
         

10.0 (28 Reviews)
House
Cozy Hillsdale Home ~ 1 Mi to Baw Beese Lake!
  • Air Conditioner
  • Parking
  • TV

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3-bedroom lake house in tranquil on Round Lake Sleeps 10 From US $182
         

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House
3-bedroom lake house in tranquil on Round Lake Sleeps 10
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Charming Lakefront 3-bedroom house, located minutes from Hillsdale College From US $238
         

10.0 (13 Reviews)
House
Charming Lakefront 3-bedroom house, located minutes from Hillsdale College
  • Air Conditioner
  • Parking
  • Pet Friendly

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A place where family memories are made. From US $336
         

10.0 (22 Reviews)
Cottage
A place where family memories are made.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lakefront, Hot Tub, Game Room Sapphire Shores From US $456
         

10.0 (5 Reviews)
House
Lakefront, Hot Tub, Game Room Sapphire Shores
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bring the Family and the pups ! Private Lakeside Home w/WIFI From US $280
         

New
Cottage
Bring the Family and the pups ! Private Lakeside Home w/WIFI
  • Parking
  • Pet Friendly
  • TV

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Lakefront Family Retreat-Great set up for multi generational families From US $863
         

10.0 (1 Review)
Cottage
Lakefront Family Retreat-Great set up for multi generational families
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sunset View on Devils Lake - Waterfront - Sleeps 10 From US $425
         

9.0 (6 Reviews)
Cottage
Sunset View on Devils Lake - Waterfront - Sleeps 10
  • Air Conditioner
  • Parking
  • TV

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Wheelchair Accessible Vacation Homes in Pittsford

Over 8+ Wheelchair Accessible Vacation Homes in or Near Pittsford
Luxury King Suite with sleeper sofa and Breakfast From US $295
         

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Hotel
Luxury King Suite with sleeper sofa and Breakfast
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Luxury King Suite with sleeper sofa and Breakfast From US $295
         

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Hotel
Luxury King Suite with sleeper sofa and Breakfast
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Executive King Room with with Modern Amenities & Breakfast From US $231
         

New
Hotel
Executive King Room with with Modern Amenities & Breakfast
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Executive King Handicap Room with Modern Amenities & Breakfast From US $235
         

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Hotel
Executive King Handicap Room with Modern Amenities & Breakfast
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Executive King Handicap Room with Modern Amenities & Breakfast From US $227
         

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Hotel
Executive King Handicap Room with Modern Amenities & Breakfast
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Executive Double Queen Room with Modern Amenities & Breakfast From US $230
         

New
Hotel
Executive Double Queen Room with Modern Amenities & Breakfast
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Executive Double Queen Room with Modern Amenities & Breakfast From US $216
         

New
Hotel
Executive Double Queen Room with Modern Amenities & Breakfast
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  • TV

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Executive King Room with with Modern Amenities & Breakfast From US $227
         

New
Hotel
Executive King Room with with Modern Amenities & Breakfast
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  • TV

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Pittsford Vacation Rentals and Airbnb Places to Stay Under $200

Over 29+ Pittsford Vacation Rentals and Airbnb Places to Stay Under $200
Charming century home in a quiet neighborhood, 3 blocks from downtown Hillsdalen From US $185
         

10.0 (13 Reviews)
House
Charming century home in a quiet neighborhood, 3 blocks from downtown Hillsdalen
  • Air Conditioner
  • Parking
  • TV

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Devil's Lake Inn and Devil's Lake Inn Too From US $138
         

9.2 (27 Reviews)
Hotel
Devil's Lake Inn and Devil's Lake Inn Too
  • Air Conditioner
  • Parking
  • Accessibility

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Sunset Acres Motel From US $85
         

8.4 (23 Reviews)
Hotel
Sunset Acres Motel
  • Parking
  • Child Friendly
  • Internet

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Charming 1-bedroom apartment with WiFi, AC in pleasant Hillsdale From US $173
         

10.0 (2 Reviews)
Apartment
Charming 1-bedroom apartment with WiFi, AC in pleasant Hillsdale
  • Air Conditioner
  • Parking
  • TV

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Full House: Hillsdale Cottage. Walking Distance to College! Across from Handmade From US $192
         

9.8 (19 Reviews)
House
Full House: Hillsdale Cottage. Walking Distance to College! Across from Handmade
  • Air Conditioner
  • Parking
  • TV

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BRB Elm Park Cottage Devils Lake Fire pit Grill Private backyard Dock From US $192
         

9.6 (10 Reviews)
Cottage
BRB Elm Park Cottage Devils Lake Fire pit Grill Private backyard Dock
  • Air Conditioner
  • Parking
  • TV

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Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College From US $83
         

8.4 (29 Reviews)
House
Heart of Hillsdale, Kitchen, Wifi, Desk, Apartment with 2 Beds Close to College
  • Air Conditioner
  • Parking
  • TV

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Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed From US $81
         

8.4 (27 Reviews)
House
Hillsdale Victorian Studio w kitchenette Wifi TV , Queen Bed and Twin Bed
  • Air Conditioner
  • TV
  • Security/Safety

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Instantly Bookable Vacation Homes in Pittsford

Over 26+ Instantly Bookable Vacation Homes in or Near Pittsford
Private Apartment in Historical Downtown Hillsdale From US $210
         

10.0 (102 Reviews)
Apartment
Private Apartment in Historical Downtown Hillsdale
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Cozy Lakefront Getaway with 3 kayaks, in Hillsdale County, Bird Lake Michigan. From US $311
         

10.0 (36 Reviews)
House
Cozy Lakefront Getaway with 3 kayaks, in Hillsdale County, Bird Lake Michigan.
  • Air Conditioner
  • Parking
  • TV

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Beautifully furnished 3-bedroom home located half a mile from Hillsdale College From US $205
         

10.0 (17 Reviews)
House
Beautifully furnished 3-bedroom home located half a mile from Hillsdale College
  • Air Conditioner
  • Parking
  • TV

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New Waterfront Guest House – Less than 10 Min to Hillsdale College From US $255
         

10.0 (8 Reviews)
House
New Waterfront Guest House – Less than 10 Min to Hillsdale College
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Charming 2-bedroom apartment in fabulous Hillsdale with WiFi, ACn From US $225
         

10.0 (2 Reviews)
Apartment
Charming 2-bedroom apartment in fabulous Hillsdale with WiFi, ACn
  • Air Conditioner
  • Parking
  • TV

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Cozy A-frame on Lime Lake From US $275
         

10.0 (1 Review)
Cottage
Cozy A-frame on Lime Lake
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Charming 3-bedroom house in Hillsdale near the College From US $206
         

9.8 (7 Reviews)
House
Charming 3-bedroom house in Hillsdale near the College
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Lake front cottage on all sports Bear Lake in Hillsdale, Michigan From US $253
         

New
Cottage
Lake front cottage on all sports Bear Lake in Hillsdale, Michigan
  • Air Conditioner
  • Parking
  • TV

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About Pittsford Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruisesbyowner Pittsford, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Pittsford. Places to stay near Pittsford with prices averaging $100 a night.

Cruisesbyowner makes it easy and safe to find and compare vacation rentals in Pittsford with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Pittsford

Type Count

Use these Quick Filters to Find a Vacation Rental in Pittsford

★ Pro Tip: Cruisesbyowner makes it easy to compare the best listings on Cruisesbyowner homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruisesbyowner homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pittsford.

Weather in Pittsford

View the weather forecast for Pittsford before booking your Pittsford Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Pittsford, MI

Cruisesbyowner offers a large selection of top attractions around Pittsford. Research things to do on your vacation before you visit Pittsford.


Michigan International Speedway Hillsdale College Devils Lake Hillsdale Hospital Baw Beese Lake Demor Hills Golf Course Harrison Lake State Park Round Lake Slayton Arboretum Stocks Park Corks Winery Richard Petty Driving Experience

Pittsford Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Pittsford?

There are a lot of options in Pittsford. If you plan on staying in the Pittsford area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pittsford:

How many vacation rentals are available in Pittsford?

Currently, the total number of properties listed in 2026 is over 1 in the Pittsford area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pittsford.