House
10.0(33 Reviews)
1 Bedroom
2 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
R6,079/Night
7 Nights - R42,554
Wellesley Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Wellesley
10.0
Apartment
8.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
Spa
Internet
Pet Friendly
R4,214/Night
7 Nights - R29,496
R34,742/Night
7 Nights - R243,198
House
10.0(6 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,276/Night
7 Nights - R43,936
House
6.0(4 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
Security/Safety
R2,698/Night
7 Nights - R18,887
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
Child Friendly
Bedding/Linens
R1,413/Night
7 Nights - R9,893
Apartment
9.2(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,905/Night
7 Nights - R34,343
House
8.6(10 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,852/Night
7 Nights - R61,974
Condo
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,343/Night
7 Nights - R16,405
Luxury Holiday Rentals in Wellesley
Over 26+ Luxury Holiday Rentals in or Near Wellesley
House
6 Bedrooms
14 Guests
- Parking
- Spa
- Balcony/Terrace
- Kitchen
R119,143/Night
7 Nights - R834,004
House
10.0(5 Reviews)
4 Bedrooms
8 Guests
Private Pool
Hot Tub
Pool- Kitchen
R94,212/Night
7 Nights - R659,492
House
10.0(2 Reviews)
3 Bedrooms
9 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R60,379/Night
7 Nights - R422,656
House
10.0(16 Reviews)
5 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R51,158/Night
7 Nights - R358,101
House
4 Bedrooms
- Hot Tub
- Air Conditioner
- Internet
- Child Friendly
R36,835/Night
7 Nights - R257,854
Villa
1 Bedroom
10 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
R29,979/Night
7 Nights - R209,854
House
1 Bedroom
8 Guests
EV Charge Station- Parking
- Air Conditioner
- Internet
R26,981/Night
7 Nights - R188,869
House
10.0(3 Reviews)
5 Bedrooms
10 Guests
- Parking
Ocean View- Balcony/Terrace
View
R16,618/Night
7 Nights - R116,336
House
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
R12,750/Night
7 Nights - R89,255
Pet-Friendly Holiday Rentals in Wellesley
Over 7+ Pet-Friendly Holiday Rentals in or Near Wellesley
Apartment
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R1,332/Night
7 Nights - R9,327
Apartment
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
R4,913/Night
7 Nights - R34,393
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R5,829/Night
7 Nights - R40,805
R10,310/Night
7 Nights - R72,167
House
4 Bedrooms
3 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
Laundry
R4,147/Night
7 Nights - R29,030
House
4.6(7 Reviews)
1 Bedroom
3 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
R2,498/Night
7 Nights - R17,488
Apartment
1 Bedroom
3 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
R1,916/Night
7 Nights - R13,407
Large Holiday Rentals and Private Villas in Wellesley
Over 2+ Large Holiday Rentals and Private Villas in or Near Wellesley
House
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R25,815/Night
7 Nights - R180,708
House
5 Bedrooms
14 Guests
R129,410/Night
7 Nights - R905,871
Wellesley Private Villas and Holiday Homes Under $200
Over 3+ Wellesley Private Villas and Holiday Homes Under $200
Apartment
10.0(90 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,170/Night
7 Nights - R22,185
House
1 Bedroom
2 Guests
- Air Conditioner
- Internet
R2,998/Night
7 Nights - R20,985
House
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Security/Safety
R2,698/Night
7 Nights - R18,887
Instantly Bookable Holiday Homes in Wellesley
Over 1+ Instantly Bookable Holiday Homes in or Near Wellesley
House
4 Bedrooms
6 Guests
- Hot Tub
- Air Conditioner
- Internet
- Laundry
R13,355/Night
7 Nights - R93,485
Book a Last Minute Place to Stay in Wellesley
About Casai's Private Villas and Holiday Rentals in Wellesley
Discover more than 35 vacation rentals available in Wellesley. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Wellesley.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Wellesley, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Wellesley. On average, places to stay near Wellesley offer 2398.23 ft², with nightly prices averaging R21,477.
With Casai, finding and comparing holiday rentals in Wellesley is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Wellesley, MA
There are 35 Wellesley, MA Holiday Rentals
- Prices for a holiday home in Wellesley start at R1,413
- Top rated vacation home in Wellesley is Lovely Studio Walk to Wellesley and Babson College
- Most popular short term in Wellesley is Lovely Studio Walk to Wellesley and Babson College
- Cheapest place to stay in Wellesley is Cozy 1 bedroom in great Wellesley location. I block from the commuter rail.
- Most expensive holiday rental in Wellesley is The Manor, A Luxury Mansion 15 min from Boston w/Large yard
Recently Booked Holiday Rentals in Wellesley
Frequently Asked Questions About Wellesley?
What are the top holiday rentals in Wellesley?
With numerous options available in Wellesley, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Wellesley:
- Lovely Studio Walk to Wellesley and Babson College
- Beautiful home in Wellesley's Historic district
- Luxury Furnished Home, Spa Bath + Steam Shower Wellesley
- Elegant Guest Suite Wellesley
- Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges.
- Minutes To Boston ~ Ideal for Day Trips To Everywhere in New England
- Quarter Finals Paradise with theatre and gym
- Cozy 1 bedroom in great Wellesley location. I block from the commuter rail.
- 1 Mi to Needham Center Square: Pet-Friendly Apt!
- Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley
Which holiday homes in Wellesley are best for families?
If you're searching for a family-friendly holiday home in Wellesley, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Wellesley:
How many Casai.co.za holiday rentals are available in Wellesley?
As of 2026, Casai boasts over 35 properties listed in the Wellesley area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Wellesley.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Wellesley Hills Vacation Rentals in Boston, Massachusetts | 42 |
| Babson Park Vacation Rentals in Boston, Massachusetts | 42 |
