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Compare 221 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

3 Bedroom Greek Revival Cottage Walk to Big House

9.4 out of 10, Exceptional, (3)
"Beautifully maintained property located in the heart of Ann Arbor and well within walking distance of U of M major stadiums. Ample parking albeit single-lane driveway; comfortable sleeping quarters in all bedroom — each complete with TV’s. Nestled among student housing, we experienced no disruption/loud noises after hours. Excellent mgmt communication avenues and reasonably priced. Will definitely book again when in Ann Arbor."
3 Bedroom Greek Revival Cottage Walk to Big House

10 min from AA - Spectacular secluded retreat

10.0 out of 10, Exceptional, (27)
"We stayed for just a few nights to celebrate the opening of our new LEGO store in town with friends and family. The home was large enough for everyone, quiet and comfortable! There are special touches everywhere and even a customized welcome when we arrived! It was a great stay and an awesome host for all of us to be under one roof!"
10 min from AA - Spectacular secluded retreat

Stylish & Private 3BR Blu Home near Univ of Michigan, Ann Arbor. Pet-Friendly!

9.2 out of 10, Wonderful, (10)
"Staying here was like staying at your best friend’s clean house in Ann Arbor. It is inviting, clean, and cozy- you feel like you can really relax and enjoy your downtime. The host has thought of everything you could possibly need as a guest and the home includes more amenities and conveniences than you could imagine. I appreciate the attention to detail and the personality infused throughout the property. The location was perfect for our family’s visit to Ann Arbor. The kids loved it, too!"
Stylish & Private 3BR Blu Home near Univ of Michigan, Ann Arbor. Pet-Friendly!

Lakefront House close to Ann Arbor!

10.0 out of 10, Exceptional, (134)
"Nice four night stay. About 15 minutes from Ann Arbor. We went to University of Michigan football game and easy to get in and get out from this area. House exactly as pictured and host has thought of everything one would need to fully feel at home here. Beautiful lake views from inside. Lovely area. Lots of leaf burning the entire time which was unfortunate as we couldn’t really enjoy being outside but that is just this time of year. Would definitely stay again. "
Lakefront House close to Ann Arbor!

Horseshoe Lake retreat- 2-bedroom + loft lake house with WiFi and AC.

2.0 star property
10.0 out of 10, Exceptional, (5)
"Surprised and welcomed with fresh veggies from owners farm and snack basket. Lovely accommodations. Very comfortable home and beautiful setting. Great communications from host and thoughtful gestures. Overall wonderful experience. Highly recommend."
Horseshoe Lake retreat- 2-bedroom + loft lake house with WiFi and AC.

3-bedroom house in Ann Arbor just across the golf course from The Big House.

3-bedroom house in Ann Arbor just across the golf course from The Big House.

Whitmore Bay: Perfect HolidayEscape Near Ann Arbor!

10.0 out of 10, Exceptional, (16)
"My husband stayed at the home, but hosted my family (12 people!) for Thanksgiving Day dinner. The home very comfortably accommodated the 8 adults playing games and watching football as well as the 4 children ranging from 2 - 12. It never felt crowded, the lay lout of the home made very part of the day smooth. The host was fantastic as well! They worked with me ahead of time to better understand what they had in their kitchen for hosting to help me plan my packing. As it turned out, they had...
Whitmore Bay: Perfect HolidayEscape Near Ann Arbor!

Cozy 3BR Westland Retreat by RedAwning

10.0 out of 10, Exceptional, (1)
"Was a good quiet place nice hosts would stay again"
Cozy 3BR Westland Retreat by RedAwning

Mark twain Great for small gatherings 5-bedroom house with WiFi 420 friendly

2.0 star property
2.0 out of 10, (1)
"I was given the wrong listing the day I would no longer be able to stay at the listing I purchased and would have to settle for a smaller listing it ruined the event I planned and my whole weekend"
Mark twain Great for small gatherings 5-bedroom house with WiFi 420 friendly

UM Football - 5 blocks to Stadium

2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely loved our stay! Very clean and conveniently located. Everything you need to enjoy your visit to Ann Arbor."
UM Football - 5 blocks to Stadium

Simple, Easy, Compact Ypsi Home

9.4 out of 10, Exceptional, (3)
"Love this part of Ypsi. Super walkable and quiet. Was great for me and my pup!"
Simple, Easy, Compact Ypsi Home

Lakefront home on 1.6 acres

9.4 out of 10, Exceptional, (68)
"Lots of space inside and outside for 3 adults and 3 children. Beautiful views of the lake from the house."
Lakefront home on 1.6 acres

Baseline Lakefront - Beautiful views, shallow swimming area - Huron chain with 7 lakes

9.8 out of 10, Exceptional, (101)
"All five stars."
Baseline Lakefront - Beautiful views, shallow swimming area - Huron chain with 7 lakes

3 bedroom 2 bathroom whole house- up to 8 people

10.0 out of 10, Exceptional, (47)
"We are return guests, because we loved our last stay. When we decided to do a girl's shopping weekend, I knew just where to stay and was glad the house was available! Jodi, the host, does a great job letting guests know about their stay. The house is impeccably clean, stocked with everything to get caffeinated in the morning, and relax after a long day out. The neighborhood is quiet but close to everything you ever need. We're already planning our 2025 excursion and will book this house...
3 bedroom 2 bathroom whole house- up to 8 people

Portage Lakefront - Great View & Location - 5 Bedrooms - 3 Baths - 2 Car Garage

9.8 out of 10, Exceptional, (92)
"Fabulous home for our large family in town for a wedding from 6 different states. Nicely clean upon arrival, beds and all furniture were very comfortable, and common areas were very conducive to catching up with family. Communication was excellent and all Interactions with Joseph (host) were very positive and he went out of his way to make sure we had everything we needed. Appreciate the extra blankets in each bedroom closet, plenty of towels even for our large family, and the iron and ironing...
Portage Lakefront - Great View & Location - 5 Bedrooms - 3 Baths - 2 Car Garage

We call it Urban Paradise- spacious home in Ypsilanti with lots of outdoor fun.

10.0 out of 10, Exceptional, (12)
"Very clean. Air conditioning was not good on top floor. Other than that it was great. "
We call it Urban Paradise- spacious home in Ypsilanti with lots of outdoor fun.

Elegant Residence 3 Miles from UM Stadium

10.0 out of 10, Exceptional, (22)
"Great neighborhood and in a great location. We came to Ann Arbor to see a Univ Mich Game and it was perfect. Close to the Stadium, stores etc. This property is well maintained and very clean. Communication with the property owner was great. No complaints"
Elegant Residence 3 Miles from UM Stadium

Updated 5 bedroom ranch w/fenced in yard and 100"+ projector near downtown!

9.8 out of 10, Exceptional, (39)
"Great place for a large family. Nice neighborhood. Great communication with property manager."
Updated 5 bedroom ranch w/fenced in yard and 100"+ projector near downtown!

Beautiful & Secluded 3BR, 1 bath with full kitchen serving Ann Arbor & Ypsilanti

10.0 out of 10, Exceptional, (47)
"Great stay! No issues or concerns. Property was very clean, up todate, and well maintained. Bedrooms were roomy and the living spaces were plenty big enough for our 6 adults. Extras onsite like little snacks, coffee selection, etc. Made for a nice touch. Only stayed 1 night for my sister's wedding. Thanks for sharing your home with us so we could attend the wedding."
The price is SAR 485
SAR 1,002 total
includes taxes & fees
27 Dec - 28 Dec
Beautiful & Secluded 3BR, 1 bath with full kitchen serving Ann Arbor & Ypsilanti

Cozy 4 bedroom home with hot tub

10.0 out of 10, Exceptional, (7)
"Great location and very clean and comfortable."
Cozy 4 bedroom home with hot tub
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 Pittsfield

10 min from AA - Spectacular secluded retreat

10.0 out of 10, Exceptional, (27)
"We stayed for just a few nights to celebrate the opening of our new LEGO store in town with friends and family. The home was large enough for everyone, quiet and comfortable! There are special touches everywhere and even a customized welcome when we arrived! It was a great stay and an awesome host for all of us to be under one roof!"
10 min from AA - Spectacular secluded retreat

A big house for your trip to the Big House. New to VRBO, 4.9 stars on others

A big house for your trip to the Big House. New to VRBO, 4.9 stars on others

Elegant Residence 3 Miles from UM Stadium

10.0 out of 10, Exceptional, (22)
"Great neighborhood and in a great location. We came to Ann Arbor to see a Univ Mich Game and it was perfect. Close to the Stadium, stores etc. This property is well maintained and very clean. Communication with the property owner was great. No complaints"
Elegant Residence 3 Miles from UM Stadium
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.