Holiday Homes in Southborough

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Featured Holiday Homes in Southborough

Peaceful 2Br House in Cambridge

2.0 star property
10.0 out of 10, Exceptional, (1)
"The location was great for us to visit our college student in Boston. Peaceful & quiet neighborhood. Our host was great in responding to any questions/issues we had."
Peaceful 2Br House in Cambridge

New 5B3B Single Family with Central AC

9.8 out of 10, Exceptional, (20)
"My parents live in town so it was lovely to have all my family to stay at this Vrbo and be able to celebrate with my Dad! The house was perfect..the rooms were spacious and the kitchen bathroom areas were so clean! The host was very accommodating and communicated with me very quickly!"
New 5B3B Single Family with Central AC

Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly

10.0 out of 10, Exceptional, (43)
"We had a wonderful stay at this beautiful house and can't wait to return. I've rarely seen such wonderful design in a house, let alone a property on VRBO. Everything was incredibly high quality. Fiona was across the way in the main house and was so helpful. My kiddos loved playing on the lawn and running through the beautiful property. We only live 45 minutes away but this felt like a real vacation. "
The price is AU$829
includes taxes & fees
25 Nov - 26 Nov
Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

9.6 out of 10, Exceptional, (19)
"Great "
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Bright & Pet-Friendly Home: 2 Mi to Harvard Square

10.0 out of 10, Exceptional, (10)
"The property was clean and well cared for - enjoyed our stay. Lots of room."
Bright & Pet-Friendly Home: 2 Mi to Harvard Square

Wonderful Renovated Family Friendly Home Close to Boston and Lexington

10.0 out of 10, Exceptional, (60)
"We enjoyed our stay and Janel was very responsive which we appreciated. The house was well appointed and our son especially enjoyed the children’s room with a “secret”closet full of books and toys. "
Wonderful Renovated Family Friendly Home Close to Boston and Lexington

Spacious vacation townhome unit with a pool

10.0 out of 10, Exceptional, (10)
"Great owners. Great neighborhood, great property. The fresh eggs were awesome!"
Spacious vacation townhome unit with a pool

Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms

10.0 out of 10, Exceptional, (1)
"Everything was spotlessly clean. The beds were comfortable, and every convenience was considered. Excellent place for a larger group—we needed 4 bedrooms—coming to town to move my son in to WPI for college. Would strongly recommend!!!"
Cozy home 5 minutes to shopping center, HC college, 2 kitchens, 2 living rooms

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

9.8 out of 10, Exceptional, (29)
"This was an amazing property! My mother stayed there and said it was cozy and she felt at home. The place was clean, cozy, and quaint! Would definitely stay there again!"
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston

6.8 out of 10, (3)
"So convenient, a great central location for our day trips Unit had everything we needed, the staff was helpful, the pool was clean and refreshing. the grounds were well maintained, "
The price is AU$263
includes taxes & fees
24 Dec - 25 Dec
1x1 Serenity in the Suburbs: Your Ideal Retreat in Westborough - Boston

Norwood Luxe Suite- Pet friendly & Commuter friendly

10.0 out of 10, Exceptional, (5)
"We had additional work to complete in Sharon, MA on a remodel project that we extended another week at Norwood for our team members, which offered them a place to unwind and recharge after long hours working. Norwood is lovely, clean and well-equipped with all the amenities. Susan is such an attentive host, it made for an all around wonderful experience. "
Norwood Luxe Suite- Pet friendly & Commuter friendly

Cozy bedrooms in Shrewsbury warm town and convenient

Cozy bedrooms in Shrewsbury warm town and convenient

Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

10.0 out of 10, Exceptional, (5)
"Very comfortable 3 bedroom house. Great location."
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

Charming 3 bedroom home Centrally located in Worcester

9.0 out of 10, Wonderful, (2)
"The home is very comfortable and good neighborhood.Bed was comfy and beding too.Would return again!"
Charming 3 bedroom home Centrally located in Worcester

Lake Access 4 Bed 3 Full Bath

10.0 out of 10, Exceptional, (14)
"Everything was great, a few suggestions, maybe provide more towels, maybe some shelving in the bathrooms to put stuff on it was pretty sparse. Otherwise we enjoyed are stay and would come back again. Thank You"
The price is AU$1,163
includes taxes & fees
1 Dec - 2 Dec
Lake Access 4 Bed 3 Full Bath

West End Deluxe Suite-Thanksgiving DEAL 🔥SAVE up to 20% Long term stays welcome!

9.8 out of 10, Exceptional, (49)
"Loved this house! Everything was perfect, easy to communicate with the owner and so clean and lovely!"
West End Deluxe Suite-Thanksgiving DEAL 🔥SAVE up to 20% Long term stays welcome!

Spacious Private Retreat Near Downtown Boston!

10.0 out of 10, Exceptional, (8)
"7 family members from Baltimore, Wawatosa, Covina and Santa Barbara shared these wonderful units and visited with with other family members who were nearby (about a mile and a half away) for four days. Very much enjoyed the visit and the accommodations......"
Spacious Private Retreat Near Downtown Boston!

105-year-old 4-bedroom Single Family Near Boston

10.0 out of 10, Exceptional, (26)
"Home was in perfect location for our needs. Quiet neighborhood and the home was comfortable and clean as well, with nice fresh towels and all kitchen amenities we needed. Coffee, tea, sugar and spices were nice to have for our use as well. Thank you!"
105-year-old 4-bedroom Single Family Near Boston

✨Private Studio w/ Loft Center Historic Carlisle✨

9.4 out of 10, Exceptional, (17)
"The space was clean and comfortable. It's on a somewhat busy road but it's not too loud. The bed was very comfortable. The only downside was that there's no way to do any cooking, there's only a mini fridge and a microwave. There's not a toaster or even a cutting board for chopping fruit/veggies. Besides this, it was an easy and comfy stay."
The price is AU$271
includes taxes & fees
1 Dec - 2 Dec
✨Private Studio w/ Loft Center Historic Carlisle✨

Spacious and luxurious 3-bedroom home w/jetted bathtub

10.0 out of 10, Exceptional, (3)
"Only caveats are the air conditioning is primitive"
Spacious and luxurious 3-bedroom home w/jetted bathtub
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 Southborough

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (951)
"Well managed and maintained. Clean and convenient. Breakfast of some sort would have been nice."
The price is AU$290
includes taxes & fees
2 Dec - 3 Dec
Crescent Suites Hotel

Residences at Solomon Pond

3.5 star property
8.0 out of 10, Very good, (134)
"Love it"
The price is AU$199
includes taxes & fees
24 Nov - 25 Nov
Residences at Solomon Pond

Lake Access 4 Bed 3 Full Bath

10.0 out of 10, Exceptional, (14)
"Everything was great, a few suggestions, maybe provide more towels, maybe some shelving in the bathrooms to put stuff on it was pretty sparse. Otherwise we enjoyed are stay and would come back again. Thank You"
The price is AU$1,163
includes taxes & fees
1 Dec - 2 Dec
Lake Access 4 Bed 3 Full Bath
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.